Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807039438/rt2007sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807039438/rt2007Isup2.hkl |
CCDC reference: 660115
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.092
- Data-to-parameter ratio = 10.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 81 PerFi PLAT112_ALERT_2_B ADDSYM Detects Additional (Pseudo) Symm. Elem... m PLAT112_ALERT_2_B ADDSYM Detects Additional (Pseudo) Symm. Elem... c PLAT112_ALERT_2_B ADDSYM Detects Additional (Pseudo) Symm. Elem... n
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 70.31 From the CIF: _reflns_number_total 1241 Count of symmetry unique reflns 766 Completeness (_total/calc) 162.01% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 475 Fraction of Friedel pairs measured 0.620 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Allen (2002); Cindrić et al. (2006); Fujita et al. (1992); Pope (1983); Pope & Mueller (1994); Rajagopal et al. (2003); Rhule et al. (1998); Yamase (1993); Yamase et al. (1996, 1999).
L-Alanine (0.18 g, 2 mmol) was added to an aqueous solution of Na2MoO4 (0.484 g, 2 mmol) and the solution was acidified by addition of HNO3 to pH 3.4. Colourless crystals of the title compound were obtained after standing for 5 days at room temperature 0.02 g, 10%). L-Alanine and Na2MoO4 were purchased from Acros Organics (Geel, Belgium).
All hydrogen atoms could be located in a difference Fourier map, and were further refined unrestrained with isotropic temperature factors fixed at 1.5 times Ueq of the parent atoms for the methyl and ammonia groups and 1.2 times Ueq of the parent atom for the H2(C2) atom.
Polyoxometalates (POMs) can be considered as oligomeric aggregates of metal cations, bridged by oxide anions that form by self-assembly processes (Rhule et al., 1998). There are two generic families of POMs, the isopolyoxometalates, that contain only d0 metal cations and oxide anions and the heteropolyoxometalates, that contain one or more p-, d-, or f-block heteroatoms in addition to the other ions (Pope, 1983; Rhule et al., 1998).
The medicinal features of these compounds cover a variety of important biological activities, such as the inhibition of specific enzymes or antiviral and antitumor activity (Pope and Mueller, 1994; Rhule et al., 1998). When used in combination with β-lactam antibiotics, polyoxotungstates enhance the antibiotic effectiveness against otherwise resistant strains of bacteria (Yamase et al., 1996). The heptamolybdate, [NH3Pri]6[Mo7O24].3H2O had shown a potent in vivo antitumor activity (Fujita, et al., 1992), which has been explained by repeated redox cycles of [Mo7O24]6- in the tumor cells (Yamase, 1993).
The biomedical investigations of polyoxomolybdates containing amino acids or even peptides (Yamase et al., 1999) have been focused upon finding polyoxomolybdates with both improved activity against cancer and clinical safety profiles.
The reported structure Na(NO3)C3H7NO2 was obtained unintentionally as the product of an attempted reaction of sodium molybdate in aqueous solution and the amino acid L-alanine, in order to obtain a γ type octamolybdate, coordinated by L-alanine Na4[Mo8O26(ala)2].18H2O (Cindrić et al., 2006). In contrast to Cindrić et al., L-alanine was used instead of D,L-alanine.
The asymmetric unit consists of one sodium and one nitrate ion and one L-alanine molecule.
The coordination geometry around the sodium atom can be considered as trigonal bipyramidal, with three bidentate nitrate anions coordinating through their oxygen atoms and two L-alanine molecules, each coordinating through one carboxyl oxygen atom (Figure 1,2).
Three nitrate anions are bidentate coordinating to the sodium atom (2.612 (2)–2.771 (2) Å), forming one plane, parallel with the (110) plane. The third nitrate oxygen atoms are coordinating to other symmetry equivalent sodium atoms, extending the plane formed. Almost perpendicular to this plane, two L-alanine molecules are coordinating to the sodium atom, each through one carboxyl oxygen atom (2.3651 (16) and 2.3891 (17) Å). The other carboxyl oxygen atoms are coordinated to sodium atoms in the planes above and beneath, respectively. Hence, infinite planes parallel with (110) are formed by the nitrate anions and the sodium atoms and these are perpendicularly linked to each other by L-alanine molecules (Figure 3).
Intermolecular hydrogen bonds are observed between N1(H1A)···O(1)[1/2 + x,-1/2 - y,2 - z] (1.92 (4) Å), N1(H1B)···O(5)[1/2 + x,1/2 - y,2 - z] (2.10 (3) Å) and N1(H1C)···O(2)[1 + x,y,z] (1.87 (4) Å) and an intramolecular hydrogen bond is found for N1(H1B)···O(2) (2.44 (3) Å).
Only four structures of alanine coordination complexes are found in the CSD (Version 5.28) (Allen, 2002). Only in one of them (Rajagopal et al., 2003), two alanine molecules are coordinated to the same cobalt ion. Concerning the nitrate ions, the reported structure is the first structure where three nitrate ions are coordinated to a sodium atom.
For related literature, see: Allen (2002); Cindrić et al. (2006); Fujita et al. (1992); Pope (1983); Pope & Mueller (1994); Rajagopal et al. (2003); Rhule et al. (1998); Yamase (1993); Yamase et al. (1996, 1999).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
[Na(NO3)(C3H7NO2)] | F(000) = 360 |
Mr = 174.10 | Dx = 1.743 Mg m−3 |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2690 reflections |
a = 5.3477 (3) Å | θ = 5.8–70.3° |
b = 9.1719 (6) Å | µ = 1.98 mm−1 |
c = 13.5284 (8) Å | T = 100 K |
V = 663.55 (7) Å3 | Rod, colourless |
Z = 4 | 0.5 × 0.3 × 0.2 mm |
Bruker SMART 6000 diffractometer | 1241 independent reflections |
Radiation source: fine-focus sealed tube | 1170 reflections with I > 2σ(I) |
Crossed Göbel mirrors monochromator | Rint = 0.048 |
ω and φ scans | θmax = 70.3°, θmin = 5.8° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −6→6 |
Tmin = 0.431, Tmax = 0.673 | k = 0→11 |
6562 measured reflections | l = 0→16 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | Only H-atom coordinates refined |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0662P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.092 | (Δ/σ)max < 0.001 |
S = 1.10 | Δρmax = 0.32 e Å−3 |
1241 reflections | Δρmin = −0.47 e Å−3 |
122 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.046 (3) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack, 1983 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.10 (12) |
[Na(NO3)(C3H7NO2)] | V = 663.55 (7) Å3 |
Mr = 174.10 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 5.3477 (3) Å | µ = 1.98 mm−1 |
b = 9.1719 (6) Å | T = 100 K |
c = 13.5284 (8) Å | 0.5 × 0.3 × 0.2 mm |
Bruker SMART 6000 diffractometer | 1241 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 1170 reflections with I > 2σ(I) |
Tmin = 0.431, Tmax = 0.673 | Rint = 0.048 |
6562 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | Only H-atom coordinates refined |
wR(F2) = 0.092 | Δρmax = 0.32 e Å−3 |
S = 1.10 | Δρmin = −0.47 e Å−3 |
1241 reflections | Absolute structure: Flack, 1983 |
122 parameters | Absolute structure parameter: 0.10 (12) |
0 restraints |
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 | ||
C1 | 0.6356 (4) | 1.05721 (19) | −0.00853 (15) | 0.0078 (4) | |
C2 | 0.3525 (4) | 1.0453 (2) | 0.00305 (15) | 0.0090 (4) | |
C3 | 0.2757 (4) | 0.8870 (2) | 0.02082 (14) | 0.0136 (4) | |
H2 | 0.300 (5) | 1.109 (3) | 0.0538 (19) | 0.016* | |
H1A | 0.247 (7) | 1.201 (3) | −0.0929 (19) | 0.020* | |
H3A | 0.322 (5) | 0.825 (3) | −0.033 (2) | 0.020* | |
H1B | 0.287 (6) | 1.064 (3) | −0.140 (2) | 0.020* | |
H3B | 0.095 (6) | 0.881 (3) | 0.028 (2) | 0.020* | |
H1C | 0.062 (6) | 1.080 (3) | −0.087 (2) | 0.020* | |
H3C | 0.348 (6) | 0.841 (3) | 0.082 (2) | 0.020* | |
N1 | 0.2284 (4) | 1.10123 (18) | −0.08786 (11) | 0.0082 (3) | |
N2 | 0.7554 (4) | 0.71413 (16) | 0.24472 (10) | 0.0087 (3) | |
Na1 | 0.75451 (17) | 1.04449 (8) | 0.23836 (5) | 0.0127 (3) | |
O1 | 0.7615 (3) | 1.09249 (14) | 0.06664 (8) | 0.0097 (3) | |
O2 | 0.7253 (3) | 1.02859 (15) | −0.09235 (10) | 0.0122 (3) | |
O3 | 0.5568 (3) | 0.7841 (2) | 0.24054 (13) | 0.0209 (4) | |
O4 | 0.9608 (3) | 0.7753 (2) | 0.23456 (13) | 0.0201 (4) | |
O5 | 0.7487 (4) | 0.57822 (15) | 0.26006 (9) | 0.0211 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0083 (9) | 0.0061 (9) | 0.0090 (9) | 0.0009 (7) | −0.0015 (8) | 0.0025 (7) |
C2 | 0.0072 (9) | 0.0125 (9) | 0.0072 (9) | −0.0007 (8) | 0.0004 (7) | −0.0005 (8) |
C3 | 0.0106 (10) | 0.0135 (9) | 0.0166 (10) | −0.0021 (10) | 0.0000 (9) | 0.0047 (7) |
N1 | 0.0056 (8) | 0.0122 (8) | 0.0067 (7) | 0.0012 (8) | 0.0001 (7) | −0.0007 (5) |
N2 | 0.0103 (8) | 0.0103 (7) | 0.0056 (7) | −0.0002 (8) | −0.0003 (8) | −0.0019 (5) |
Na1 | 0.0135 (4) | 0.0164 (4) | 0.0084 (4) | −0.0005 (4) | −0.0010 (4) | 0.0027 (2) |
O1 | 0.0089 (6) | 0.0119 (6) | 0.0082 (6) | 0.0011 (7) | −0.0022 (7) | −0.0005 (4) |
O2 | 0.0086 (7) | 0.0214 (8) | 0.0067 (6) | 0.0002 (7) | 0.0014 (6) | −0.0014 (5) |
O3 | 0.0142 (8) | 0.0329 (9) | 0.0157 (8) | 0.0120 (7) | −0.0030 (7) | −0.0045 (9) |
O4 | 0.0142 (8) | 0.0264 (8) | 0.0197 (9) | −0.0095 (7) | 0.0053 (7) | −0.0051 (7) |
O5 | 0.0418 (10) | 0.0106 (7) | 0.0108 (6) | −0.0020 (9) | 0.0036 (9) | −0.0012 (5) |
C1—O2 | 1.259 (3) | N1—H1B | 0.84 (3) |
C1—O1 | 1.262 (2) | N1—H1C | 0.91 (3) |
C1—C2 | 1.526 (3) | N2—O4 | 1.241 (3) |
C2—N1 | 1.489 (2) | N2—O3 | 1.242 (3) |
C2—C3 | 1.528 (3) | N2—O5 | 1.264 (2) |
C2—H2 | 0.94 (3) | N2—Na1 | 3.0312 (17) |
C3—H3A | 0.96 (3) | Na1—O1 | 2.3647 (13) |
C3—H3B | 0.97 (3) | Na1—O3 | 2.612 (2) |
C3—H3C | 1.00 (3) | Na1—O4 | 2.705 (2) |
N1—H1A | 0.92 (3) | ||
O2—C1—O1 | 125.16 (19) | C2—N1—H1C | 110.9 (19) |
O2—C1—C2 | 117.11 (17) | H1A—N1—H1C | 108 (3) |
O1—C1—C2 | 117.72 (17) | H1B—N1—H1C | 106 (3) |
N1—C2—C1 | 109.44 (16) | O4—N2—O3 | 121.22 (17) |
N1—C2—C3 | 109.74 (16) | O4—N2—O5 | 119.3 (2) |
C1—C2—C3 | 110.54 (17) | O3—N2—O5 | 119.5 (2) |
N1—C2—H2 | 104.8 (17) | O4—N2—Na1 | 63.02 (11) |
C1—C2—H2 | 109.2 (17) | O3—N2—Na1 | 58.74 (12) |
C3—C2—H2 | 112.9 (17) | O5—N2—Na1 | 171.99 (11) |
C2—C3—H3A | 111.7 (17) | O1—Na1—O3 | 100.82 (6) |
C2—C3—H3B | 109.6 (18) | O1—Na1—O4 | 98.33 (6) |
H3A—C3—H3B | 108 (2) | O3—Na1—O4 | 47.99 (5) |
C2—C3—H3C | 115.1 (16) | O1—Na1—N2 | 102.35 (5) |
H3A—C3—H3C | 106 (2) | O3—Na1—N2 | 23.98 (6) |
H3B—C3—H3C | 106 (2) | O4—Na1—N2 | 24.14 (6) |
C2—N1—H1A | 110.8 (18) | C1—O1—Na1 | 137.35 (13) |
C2—N1—H1B | 112.4 (19) | N2—O3—Na1 | 97.28 (13) |
H1A—N1—H1B | 108 (3) | N2—O4—Na1 | 92.84 (13) |
Experimental details
Crystal data | |
Chemical formula | [Na(NO3)(C3H7NO2)] |
Mr | 174.10 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 100 |
a, b, c (Å) | 5.3477 (3), 9.1719 (6), 13.5284 (8) |
V (Å3) | 663.55 (7) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 1.98 |
Crystal size (mm) | 0.5 × 0.3 × 0.2 |
Data collection | |
Diffractometer | Bruker SMART 6000 |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.431, 0.673 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6562, 1241, 1170 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.611 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.092, 1.10 |
No. of reflections | 1241 |
No. of parameters | 122 |
H-atom treatment | Only H-atom coordinates refined |
Δρmax, Δρmin (e Å−3) | 0.32, −0.47 |
Absolute structure | Flack, 1983 |
Absolute structure parameter | 0.10 (12) |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.
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Polyoxometalates (POMs) can be considered as oligomeric aggregates of metal cations, bridged by oxide anions that form by self-assembly processes (Rhule et al., 1998). There are two generic families of POMs, the isopolyoxometalates, that contain only d0 metal cations and oxide anions and the heteropolyoxometalates, that contain one or more p-, d-, or f-block heteroatoms in addition to the other ions (Pope, 1983; Rhule et al., 1998).
The medicinal features of these compounds cover a variety of important biological activities, such as the inhibition of specific enzymes or antiviral and antitumor activity (Pope and Mueller, 1994; Rhule et al., 1998). When used in combination with β-lactam antibiotics, polyoxotungstates enhance the antibiotic effectiveness against otherwise resistant strains of bacteria (Yamase et al., 1996). The heptamolybdate, [NH3Pri]6[Mo7O24].3H2O had shown a potent in vivo antitumor activity (Fujita, et al., 1992), which has been explained by repeated redox cycles of [Mo7O24]6- in the tumor cells (Yamase, 1993).
The biomedical investigations of polyoxomolybdates containing amino acids or even peptides (Yamase et al., 1999) have been focused upon finding polyoxomolybdates with both improved activity against cancer and clinical safety profiles.
The reported structure Na(NO3)C3H7NO2 was obtained unintentionally as the product of an attempted reaction of sodium molybdate in aqueous solution and the amino acid L-alanine, in order to obtain a γ type octamolybdate, coordinated by L-alanine Na4[Mo8O26(ala)2].18H2O (Cindrić et al., 2006). In contrast to Cindrić et al., L-alanine was used instead of D,L-alanine.
The asymmetric unit consists of one sodium and one nitrate ion and one L-alanine molecule.
The coordination geometry around the sodium atom can be considered as trigonal bipyramidal, with three bidentate nitrate anions coordinating through their oxygen atoms and two L-alanine molecules, each coordinating through one carboxyl oxygen atom (Figure 1,2).
Three nitrate anions are bidentate coordinating to the sodium atom (2.612 (2)–2.771 (2) Å), forming one plane, parallel with the (110) plane. The third nitrate oxygen atoms are coordinating to other symmetry equivalent sodium atoms, extending the plane formed. Almost perpendicular to this plane, two L-alanine molecules are coordinating to the sodium atom, each through one carboxyl oxygen atom (2.3651 (16) and 2.3891 (17) Å). The other carboxyl oxygen atoms are coordinated to sodium atoms in the planes above and beneath, respectively. Hence, infinite planes parallel with (110) are formed by the nitrate anions and the sodium atoms and these are perpendicularly linked to each other by L-alanine molecules (Figure 3).
Intermolecular hydrogen bonds are observed between N1(H1A)···O(1)[1/2 + x,-1/2 - y,2 - z] (1.92 (4) Å), N1(H1B)···O(5)[1/2 + x,1/2 - y,2 - z] (2.10 (3) Å) and N1(H1C)···O(2)[1 + x,y,z] (1.87 (4) Å) and an intramolecular hydrogen bond is found for N1(H1B)···O(2) (2.44 (3) Å).
Only four structures of alanine coordination complexes are found in the CSD (Version 5.28) (Allen, 2002). Only in one of them (Rajagopal et al., 2003), two alanine molecules are coordinated to the same cobalt ion. Concerning the nitrate ions, the reported structure is the first structure where three nitrate ions are coordinated to a sodium atom.