Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041735/rz6152sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041735/rz6152Isup2.hkl |
CCDC reference: 296643
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.048
- wR factor = 0.137
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
A mixture of pyridine-2,6-dicarboxylic acid (1.0 g, 6.0 mmol) and thionyl chloride (3 ml) was refluxed for 3 h. To this solution, 2-azidoethanol (1.5 g, 13.2 mmol) and triethylamine (1.84 ml, 13.2 mmol) in dry CH2Cl2 (15 ml) were added. The mixture was stirred overnight at 323 K and then filtered. Evaporation of the solvent left a crude yellow solid, followed by chromatographic purification on a silica-gel column with ethyl acetate–petroleum ether (1:8 v/v) as eluants. Colorless single crystals suitable for X-ray crystallographic analysis were grown by slow evaporation of an ethyl acetate solution.
All H atoms were located in difference Fourier maps and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C11H11N7O4 | F(000) = 632 |
Mr = 305.27 | Dx = 1.424 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1833 reflections |
a = 14.407 (3) Å | θ = 2.3–25.6° |
b = 11.854 (3) Å | µ = 0.11 mm−1 |
c = 8.942 (2) Å | T = 293 K |
β = 111.142 (3)° | Needle, colorless |
V = 1424.3 (6) Å3 | 0.36 × 0.14 × 0.11 mm |
Z = 4 |
Siemens SMART 1000 CCD area-detector diffractometer | 1416 independent reflections |
Radiation source: fine-focus sealed tube | 1233 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.1°, θmin = 2.3° |
ω scans | h = −16→17 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −14→10 |
Tmin = 0.961, Tmax = 0.988 | l = −11→10 |
4299 measured reflections |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0749P)2 + 0.6085P] where P = (Fo2 + 2Fc2)/3 |
1416 reflections | (Δ/σ)max < 0.001 |
101 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C11H11N7O4 | V = 1424.3 (6) Å3 |
Mr = 305.27 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 14.407 (3) Å | µ = 0.11 mm−1 |
b = 11.854 (3) Å | T = 293 K |
c = 8.942 (2) Å | 0.36 × 0.14 × 0.11 mm |
β = 111.142 (3)° |
Siemens SMART 1000 CCD area-detector diffractometer | 1416 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1233 reflections with I > 2σ(I) |
Tmin = 0.961, Tmax = 0.988 | Rint = 0.017 |
4299 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.20 e Å−3 |
1416 reflections | Δρmin = −0.24 e Å−3 |
101 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 | 0.19434 (13) | 0.30279 (12) | 0.62244 (19) | 0.0888 (6) | |
O2 | 0.10863 (8) | 0.14788 (9) | 0.51612 (12) | 0.0494 (3) | |
N1 | 0.13452 (17) | −0.09088 (15) | 0.5125 (2) | 0.0800 (6) | |
N2 | 0.13037 (14) | −0.19311 (15) | 0.5167 (2) | 0.0676 (5) | |
N3 | 0.1290 (2) | −0.28773 (18) | 0.5058 (3) | 0.0996 (8) | |
N4 | 0.0000 | 0.25984 (14) | 0.2500 | 0.0425 (5) | |
C1 | 0.0000 | 0.4952 (2) | 0.2500 | 0.0713 (8) | |
H1A | 0.0000 | 0.5736 | 0.2500 | 0.086* | |
C2 | 0.06356 (15) | 0.43658 (15) | 0.3780 (2) | 0.0617 (5) | |
H2A | 0.1078 | 0.4745 | 0.4658 | 0.074* | |
C3 | 0.06074 (12) | 0.31924 (13) | 0.37417 (19) | 0.0461 (4) | |
C4 | 0.12839 (13) | 0.25668 (14) | 0.51653 (19) | 0.0503 (4) | |
C5 | 0.17262 (14) | 0.08486 (16) | 0.6543 (2) | 0.0584 (5) | |
H5A | 0.1775 | 0.1237 | 0.7523 | 0.070* | |
H5B | 0.2389 | 0.0787 | 0.6507 | 0.070* | |
C6 | 0.12965 (13) | −0.02960 (14) | 0.6518 (2) | 0.0514 (4) | |
H6A | 0.1670 | −0.0698 | 0.7496 | 0.062* | |
H6B | 0.0611 | −0.0235 | 0.6448 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0998 (12) | 0.0640 (9) | 0.0689 (10) | −0.0301 (8) | −0.0103 (9) | −0.0078 (7) |
O2 | 0.0558 (7) | 0.0426 (7) | 0.0392 (6) | −0.0082 (5) | 0.0044 (5) | 0.0021 (5) |
N1 | 0.1328 (17) | 0.0522 (10) | 0.0686 (11) | 0.0154 (10) | 0.0529 (12) | 0.0094 (8) |
N2 | 0.0789 (12) | 0.0604 (11) | 0.0695 (11) | 0.0004 (8) | 0.0338 (9) | −0.0042 (8) |
N3 | 0.133 (2) | 0.0617 (13) | 0.118 (2) | −0.0143 (12) | 0.0617 (17) | −0.0204 (12) |
N4 | 0.0517 (10) | 0.0335 (9) | 0.0433 (10) | 0.000 | 0.0182 (8) | 0.000 |
C1 | 0.100 (2) | 0.0307 (12) | 0.082 (2) | 0.000 | 0.0311 (17) | 0.000 |
C2 | 0.0808 (13) | 0.0390 (9) | 0.0654 (12) | −0.0103 (8) | 0.0265 (10) | −0.0108 (8) |
C3 | 0.0561 (9) | 0.0374 (8) | 0.0473 (9) | −0.0065 (6) | 0.0220 (8) | −0.0054 (6) |
C4 | 0.0584 (10) | 0.0442 (9) | 0.0445 (9) | −0.0117 (7) | 0.0138 (8) | −0.0076 (7) |
C5 | 0.0554 (10) | 0.0650 (12) | 0.0416 (9) | −0.0053 (8) | 0.0016 (7) | 0.0077 (8) |
C6 | 0.0592 (10) | 0.0507 (10) | 0.0412 (9) | 0.0067 (7) | 0.0142 (7) | 0.0098 (7) |
O1—C4 | 1.204 (2) | C1—H1A | 0.9300 |
O2—C4 | 1.321 (2) | C2—C3 | 1.392 (2) |
O2—C5 | 1.453 (2) | C2—H2A | 0.9300 |
N1—N2 | 1.215 (2) | C3—C4 | 1.492 (2) |
N1—C6 | 1.465 (2) | C5—C6 | 1.488 (3) |
N2—N3 | 1.125 (2) | C5—H5A | 0.9700 |
N4—C3 | 1.3392 (18) | C5—H5B | 0.9700 |
N4—C3i | 1.3392 (18) | C6—H6A | 0.9700 |
C1—C2i | 1.369 (2) | C6—H6B | 0.9700 |
C1—C2 | 1.369 (2) | ||
C4—O2—C5 | 115.45 (12) | O1—C4—C3 | 122.21 (16) |
N2—N1—C6 | 116.77 (16) | O2—C4—C3 | 114.16 (13) |
N3—N2—N1 | 172.4 (2) | O2—C5—C6 | 108.86 (13) |
C3—N4—C3i | 116.56 (19) | O2—C5—H5A | 109.9 |
C2i—C1—C2 | 119.0 (2) | C6—C5—H5A | 109.9 |
C2i—C1—H1A | 120.5 | O2—C5—H5B | 109.9 |
C2—C1—H1A | 120.5 | C6—C5—H5B | 109.9 |
C1—C2—C3 | 118.82 (18) | H5A—C5—H5B | 108.3 |
C1—C2—H2A | 120.6 | N1—C6—C5 | 108.50 (15) |
C3—C2—H2A | 120.6 | N1—C6—H6A | 110.0 |
N4—C3—C2 | 123.39 (16) | C5—C6—H6A | 110.0 |
N4—C3—C4 | 118.46 (14) | N1—C6—H6B | 110.0 |
C2—C3—C4 | 118.14 (15) | C5—C6—H6B | 110.0 |
O1—C4—O2 | 123.63 (17) | H6A—C6—H6B | 108.4 |
C2i—C1—C2—C3 | −0.57 (11) | N4—C3—C4—O1 | 169.43 (17) |
C3i—N4—C3—C2 | −0.62 (13) | C2—C3—C4—O1 | −11.1 (3) |
C3i—N4—C3—C4 | 178.86 (16) | N4—C3—C4—O2 | −11.3 (2) |
C1—C2—C3—N4 | 1.2 (2) | C2—C3—C4—O2 | 168.23 (15) |
C1—C2—C3—C4 | −178.26 (14) | C4—O2—C5—C6 | 169.33 (14) |
C5—O2—C4—O1 | −0.1 (3) | N2—N1—C6—C5 | 159.13 (19) |
C5—O2—C4—C3 | −179.33 (14) | O2—C5—C6—N1 | 66.4 (2) |
Symmetry code: (i) −x, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6A···O1ii | 0.97 | 2.44 | 3.280 (3) | 145 |
Symmetry code: (ii) −x+1/2, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C11H11N7O4 |
Mr | 305.27 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 14.407 (3), 11.854 (3), 8.942 (2) |
β (°) | 111.142 (3) |
V (Å3) | 1424.3 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.36 × 0.14 × 0.11 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.961, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4299, 1416, 1233 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.619 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.137, 1.06 |
No. of reflections | 1416 |
No. of parameters | 101 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.24 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
O1—C4 | 1.204 (2) | N1—N2 | 1.215 (2) |
O2—C4 | 1.321 (2) | N1—C6 | 1.465 (2) |
O2—C5 | 1.453 (2) | N2—N3 | 1.125 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6A···O1i | 0.97 | 2.44 | 3.280 (3) | 145 |
Symmetry code: (i) −x+1/2, y−1/2, −z+3/2. |
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Azides are used to synthesize triazole or tetrazole derivatives, which frequently exhibit significant biological activity and, in consequence, have found a wide variety of applications as active heterocycles in pharmacy and agriculture (Ostrovskii & Koren, 2000; Nomiya et al., 2000). In addition, photolysis of azide leads to the formation of azido radicals, which are employed in the photoinitiation of radical polymerization industrially (Endicott et al., 1970). In an attempt to synthesize new triazoles or tetrazoles, the title compound, (I), was synthesized and its structure is reported here.
The asymmetric unit of (I) contains one half-molecule, the other half being related by a crystallographic twofold axis passing through the C1···N4 line. The bond lengths and angles in (I) show normal values (Allen et al., 1987). The molecule is not planar, the two side chains twisting from the mean plane of pyridine ring in opposite directions. In the packing of the title compound, molecules are linked into two-dimensional layers perpendicular to the a axis (Fig. 2) by C6—H6A···O1 intermolecular hydrogen bonds. These interactions, together with van der Waals forces, stabilize the crystal structure.