Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051379/hb2590sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051379/hb2590Isup2.hkl |
CCDC reference: 667434
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.126
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 5 Informative message, check
The title compound was prepared according to the method of Huang & Tzai (1986). Colourless prism of (I) were obtained by recrystallization from ethyl acetate.
All the H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Kentene aminals with an imidazolidine ring can act as nucleophiles and they are useful synthons, especially for the synthesis of fused heterocycles (Huang & Tzai, 1986). The title compound, (I), (Fig. 1), is an important representative of such reagents.
As shown in Fig. 1, the pyridine ring and the imidazolidine ring are nearly in the same plane [dihedral angle = 4.88 (12)°]. The crystal structure is stabilized by weak C—H···O intermolecular interactions (Table 1).
For the synthesis, see: Huang & Tzai (1986).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).
Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. |
C10H11N3O5 | F(000) = 528 |
Mr = 253.22 | Dx = 1.479 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2092 reflections |
a = 9.848 (5) Å | θ = 2.7–25.7° |
b = 10.738 (5) Å | µ = 0.12 mm−1 |
c = 11.318 (6) Å | T = 294 K |
β = 108.165 (8)° | Prism, colorless |
V = 1137.2 (10) Å3 | 0.22 × 0.20 × 0.14 mm |
Z = 4 |
Bruker SMART 1000 CCD diffractometer | 2008 independent reflections |
Radiation source: fine-focus sealed tube | 1428 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω scans | θmax = 25.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→11 |
Tmin = 0.974, Tmax = 0.983 | k = −10→12 |
5593 measured reflections | l = −13→13 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0642P)2 + 0.3776P] where P = (Fo2 + 2Fc2)/3 |
2008 reflections | (Δ/σ)max = 0.008 |
165 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C10H11N3O5 | V = 1137.2 (10) Å3 |
Mr = 253.22 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.848 (5) Å | µ = 0.12 mm−1 |
b = 10.738 (5) Å | T = 294 K |
c = 11.318 (6) Å | 0.22 × 0.20 × 0.14 mm |
β = 108.165 (8)° |
Bruker SMART 1000 CCD diffractometer | 2008 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1428 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.983 | Rint = 0.030 |
5593 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.21 e Å−3 |
2008 reflections | Δρmin = −0.23 e Å−3 |
165 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 | 0.4168 (2) | 0.36676 (18) | 0.40827 (18) | 0.0638 (6) | |
O2 | 0.5293 (2) | 0.2252 (2) | 0.33881 (18) | 0.0691 (6) | |
O3 | 0.30450 (17) | 0.10139 (14) | 0.15771 (13) | 0.0430 (4) | |
O4 | 0.4560 (2) | −0.0553 (2) | 0.23765 (17) | 0.0732 (7) | |
O5 | 0.12662 (17) | −0.10383 (14) | 0.53454 (15) | 0.0464 (5) | |
N1 | 0.34353 (19) | 0.26613 (16) | 0.62403 (16) | 0.0347 (4) | |
N2 | 0.23172 (18) | 0.08686 (16) | 0.55925 (15) | 0.0322 (4) | |
N3 | 0.4424 (2) | 0.2564 (2) | 0.39231 (17) | 0.0432 (5) | |
C1 | 0.4703 (3) | 0.3461 (2) | 0.6653 (2) | 0.0476 (6) | |
H1A | 0.5492 | 0.3056 | 0.6483 | 0.071* | |
H1B | 0.4937 | 0.3610 | 0.7530 | 0.071* | |
H1C | 0.4510 | 0.4239 | 0.6215 | 0.071* | |
C2 | 0.2644 (3) | 0.2399 (2) | 0.7117 (2) | 0.0550 (7) | |
H2A | 0.1934 | 0.3039 | 0.7071 | 0.066* | |
H2B | 0.3289 | 0.2361 | 0.7962 | 0.066* | |
C3 | 0.1939 (3) | 0.1156 (2) | 0.6725 (2) | 0.0439 (6) | |
H3A | 0.2313 | 0.0531 | 0.7362 | 0.053* | |
H3B | 0.0912 | 0.1213 | 0.6546 | 0.053* | |
C4 | 0.3190 (2) | 0.17757 (19) | 0.53658 (18) | 0.0282 (5) | |
C5 | 0.3675 (2) | 0.16054 (19) | 0.43311 (19) | 0.0317 (5) | |
C6 | 0.3348 (2) | 0.0470 (2) | 0.36515 (19) | 0.0343 (5) | |
C7 | 0.2556 (3) | −0.0434 (2) | 0.3964 (2) | 0.0389 (6) | |
H7 | 0.2375 | −0.1171 | 0.3510 | 0.047* | |
C8 | 0.1991 (2) | −0.0271 (2) | 0.49896 (19) | 0.0348 (5) | |
C9 | 0.3759 (2) | 0.0253 (2) | 0.2483 (2) | 0.0398 (6) | |
C10 | 0.3298 (3) | 0.0872 (3) | 0.0386 (2) | 0.0587 (8) | |
H10A | 0.4256 | 0.1126 | 0.0464 | 0.088* | |
H10B | 0.2634 | 0.1380 | −0.0225 | 0.088* | |
H10C | 0.3171 | 0.0015 | 0.0133 | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0873 (14) | 0.0420 (11) | 0.0701 (13) | −0.0070 (10) | 0.0361 (11) | 0.0132 (10) |
O2 | 0.0657 (12) | 0.0934 (15) | 0.0666 (12) | −0.0229 (11) | 0.0473 (11) | −0.0131 (11) |
O3 | 0.0539 (10) | 0.0478 (10) | 0.0311 (8) | 0.0149 (8) | 0.0187 (8) | 0.0060 (7) |
O4 | 0.0920 (15) | 0.0826 (14) | 0.0534 (12) | 0.0525 (12) | 0.0349 (11) | 0.0129 (10) |
O5 | 0.0532 (10) | 0.0394 (9) | 0.0463 (10) | −0.0144 (8) | 0.0150 (8) | 0.0045 (7) |
N1 | 0.0362 (10) | 0.0341 (10) | 0.0381 (10) | −0.0070 (8) | 0.0176 (8) | −0.0048 (8) |
N2 | 0.0365 (10) | 0.0342 (10) | 0.0290 (9) | −0.0074 (8) | 0.0147 (8) | −0.0019 (8) |
N3 | 0.0441 (12) | 0.0528 (14) | 0.0368 (10) | −0.0067 (10) | 0.0186 (9) | 0.0060 (10) |
C1 | 0.0478 (15) | 0.0433 (15) | 0.0534 (15) | −0.0141 (11) | 0.0183 (12) | −0.0086 (12) |
C2 | 0.0684 (17) | 0.0590 (17) | 0.0527 (15) | −0.0210 (14) | 0.0408 (14) | −0.0200 (13) |
C3 | 0.0510 (14) | 0.0535 (15) | 0.0349 (12) | −0.0144 (12) | 0.0247 (11) | −0.0079 (11) |
C4 | 0.0271 (11) | 0.0282 (11) | 0.0291 (10) | 0.0016 (8) | 0.0086 (9) | 0.0032 (9) |
C5 | 0.0320 (12) | 0.0349 (12) | 0.0306 (11) | 0.0006 (9) | 0.0132 (9) | 0.0056 (10) |
C6 | 0.0351 (12) | 0.0390 (13) | 0.0289 (11) | 0.0107 (10) | 0.0103 (10) | 0.0046 (10) |
C7 | 0.0518 (14) | 0.0315 (12) | 0.0322 (12) | 0.0015 (10) | 0.0113 (10) | −0.0030 (10) |
C8 | 0.0373 (12) | 0.0331 (12) | 0.0309 (11) | −0.0019 (10) | 0.0058 (10) | 0.0030 (10) |
C9 | 0.0448 (13) | 0.0429 (14) | 0.0342 (12) | 0.0125 (11) | 0.0159 (11) | 0.0024 (11) |
C10 | 0.080 (2) | 0.0701 (19) | 0.0337 (13) | 0.0084 (15) | 0.0291 (14) | 0.0059 (13) |
O1—N3 | 1.237 (3) | C1—H1C | 0.9600 |
O2—N3 | 1.239 (2) | C2—C3 | 1.506 (3) |
O3—C9 | 1.328 (3) | C2—H2A | 0.9700 |
O3—C10 | 1.453 (3) | C2—H2B | 0.9700 |
O4—C9 | 1.203 (3) | C3—H3A | 0.9700 |
O5—C8 | 1.236 (2) | C3—H3B | 0.9700 |
N1—C4 | 1.339 (3) | C4—C5 | 1.408 (3) |
N1—C1 | 1.466 (3) | C5—C6 | 1.424 (3) |
N1—C2 | 1.467 (3) | C6—C7 | 1.359 (3) |
N2—C4 | 1.375 (3) | C6—C9 | 1.516 (3) |
N2—C8 | 1.390 (3) | C7—C8 | 1.446 (3) |
N2—C3 | 1.474 (3) | C7—H7 | 0.9300 |
N3—C5 | 1.424 (3) | C10—H10A | 0.9600 |
C1—H1A | 0.9600 | C10—H10B | 0.9600 |
C1—H1B | 0.9600 | C10—H10C | 0.9600 |
C9—O3—C10 | 116.69 (18) | C2—C3—H3B | 111.2 |
C4—N1—C1 | 126.18 (18) | H3A—C3—H3B | 109.1 |
C4—N1—C2 | 110.63 (17) | N1—C4—N2 | 110.13 (17) |
C1—N1—C2 | 118.42 (18) | N1—C4—C5 | 132.64 (19) |
C4—N2—C8 | 126.48 (17) | N2—C4—C5 | 117.20 (19) |
C4—N2—C3 | 110.84 (17) | C4—C5—C6 | 118.85 (19) |
C8—N2—C3 | 121.94 (17) | C4—C5—N3 | 121.3 (2) |
O1—N3—O2 | 122.2 (2) | C6—C5—N3 | 119.75 (18) |
O1—N3—C5 | 119.69 (19) | C7—C6—C5 | 121.50 (19) |
O2—N3—C5 | 118.0 (2) | C7—C6—C9 | 116.6 (2) |
N1—C1—H1A | 109.5 | C5—C6—C9 | 121.67 (19) |
N1—C1—H1B | 109.5 | C6—C7—C8 | 121.2 (2) |
H1A—C1—H1B | 109.5 | C6—C7—H7 | 119.4 |
N1—C1—H1C | 109.5 | C8—C7—H7 | 119.4 |
H1A—C1—H1C | 109.5 | O5—C8—N2 | 119.68 (19) |
H1B—C1—H1C | 109.5 | O5—C8—C7 | 125.9 (2) |
N1—C2—C3 | 105.29 (17) | N2—C8—C7 | 114.39 (18) |
N1—C2—H2A | 110.7 | O4—C9—O3 | 124.8 (2) |
C3—C2—H2A | 110.7 | O4—C9—C6 | 124.0 (2) |
N1—C2—H2B | 110.7 | O3—C9—C6 | 111.00 (18) |
C3—C2—H2B | 110.7 | O3—C10—H10A | 109.5 |
H2A—C2—H2B | 108.8 | O3—C10—H10B | 109.5 |
N2—C3—C2 | 102.93 (17) | H10A—C10—H10B | 109.5 |
N2—C3—H3A | 111.2 | O3—C10—H10C | 109.5 |
C2—C3—H3A | 111.2 | H10A—C10—H10C | 109.5 |
N2—C3—H3B | 111.2 | H10B—C10—H10C | 109.5 |
C4—N1—C2—C3 | 4.1 (3) | O2—N3—C5—C6 | −31.4 (3) |
C1—N1—C2—C3 | −153.0 (2) | C4—C5—C6—C7 | 1.5 (3) |
C4—N2—C3—C2 | 2.8 (3) | N3—C5—C6—C7 | −175.7 (2) |
C8—N2—C3—C2 | 173.6 (2) | C4—C5—C6—C9 | 176.32 (19) |
N1—C2—C3—N2 | −4.0 (3) | N3—C5—C6—C9 | −0.9 (3) |
C1—N1—C4—N2 | 152.4 (2) | C5—C6—C7—C8 | 1.0 (3) |
C2—N1—C4—N2 | −2.4 (2) | C9—C6—C7—C8 | −174.04 (19) |
C1—N1—C4—C5 | −25.7 (4) | C4—N2—C8—O5 | 175.04 (19) |
C2—N1—C4—C5 | 179.4 (2) | C3—N2—C8—O5 | 5.8 (3) |
C8—N2—C4—N1 | −170.60 (19) | C4—N2—C8—C7 | −5.3 (3) |
C3—N2—C4—N1 | −0.3 (2) | C3—N2—C8—C7 | −174.6 (2) |
C8—N2—C4—C5 | 7.9 (3) | C6—C7—C8—O5 | −179.8 (2) |
C3—N2—C4—C5 | 178.12 (19) | C6—C7—C8—N2 | 0.6 (3) |
N1—C4—C5—C6 | 172.5 (2) | C10—O3—C9—O4 | −2.0 (4) |
N2—C4—C5—C6 | −5.5 (3) | C10—O3—C9—C6 | −177.7 (2) |
N1—C4—C5—N3 | −10.3 (4) | C7—C6—C9—O4 | −66.8 (3) |
N2—C4—C5—N3 | 171.63 (18) | C5—C6—C9—O4 | 118.1 (3) |
O1—N3—C5—C4 | −30.2 (3) | C7—C6—C9—O3 | 108.9 (2) |
O2—N3—C5—C4 | 151.5 (2) | C5—C6—C9—O3 | −66.1 (3) |
O1—N3—C5—C6 | 146.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O2i | 0.97 | 2.54 | 3.106 (4) | 118 |
C2—H2B···O5ii | 0.97 | 2.51 | 3.209 (3) | 129 |
C3—H3B···O5iii | 0.97 | 2.52 | 3.295 (4) | 137 |
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) −x+1/2, y+1/2, −z+3/2; (iii) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C10H11N3O5 |
Mr | 253.22 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 9.848 (5), 10.738 (5), 11.318 (6) |
β (°) | 108.165 (8) |
V (Å3) | 1137.2 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.22 × 0.20 × 0.14 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.974, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5593, 2008, 1428 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.126, 1.04 |
No. of reflections | 2008 |
No. of parameters | 165 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.23 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O2i | 0.97 | 2.54 | 3.106 (4) | 118 |
C2—H2B···O5ii | 0.97 | 2.51 | 3.209 (3) | 129 |
C3—H3B···O5iii | 0.97 | 2.52 | 3.295 (4) | 137 |
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) −x+1/2, y+1/2, −z+3/2; (iii) −x, −y, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
Kentene aminals with an imidazolidine ring can act as nucleophiles and they are useful synthons, especially for the synthesis of fused heterocycles (Huang & Tzai, 1986). The title compound, (I), (Fig. 1), is an important representative of such reagents.
As shown in Fig. 1, the pyridine ring and the imidazolidine ring are nearly in the same plane [dihedral angle = 4.88 (12)°]. The crystal structure is stabilized by weak C—H···O intermolecular interactions (Table 1).