Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801020104/ob6096sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801020104/ob6096Isup2.hkl |
CCDC reference: 177236
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.056
- wR factor = 0.189
- Data-to-parameter ratio = 14.0
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level A:
PLAT_706 Alert A H...A Calc 13.48(3), Rep 2.09(4), Dev. 379.67 Sigma H1' -O2 1.555 1.545 PLAT_706 Alert A H...A Calc 8.00(4), Rep 1.81(5), Dev. 154.75 Sigma H2' -N2 1.555 2.555 PLAT_707 Alert A D...A Calc 13.002(4), Rep 2.889(3), Dev. 2528.25 Sigma O1 -O2 1.555 1.545 PLAT_707 Alert A D...A Calc 8.254(3), Rep 2.742(3), Dev. 1837.33 Sigma O2 -N2 1.555 2.555 PLAT_708 Alert A D-H..A Calc 55(2), Rep 154(3), Dev. 49.50 Sigma O1 -H1' -O2 1.555 1.555 1.545 PLAT_708 Alert A D-H..A Calc 103(2), Rep 174(4), Dev. 35.50 Sigma O2 -H2' -N2 1.555 1.555 2.555 PLAT_737 Alert A D...A Calc 2.529(3), Rep 2.53(3) .... 9.90 s.u-Ratio N1 -O1 1.555 1.555
7 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
0 Alert Level C = Please check
Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C11H15N3O2 | F(000) = 472 |
Mr = 221.26 | Dx = 1.328 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 8.404 (2) Å | θ = 10–18° |
b = 7.672 (2) Å | µ = 0.09 mm−1 |
c = 17.592 (3) Å | T = 296 K |
β = 102.620 (19)° | Prism, colorless |
V = 1106.8 (4) Å3 | 0.35 × 0.15 × 0.15 mm |
Z = 4 |
Enraf-Nonius Turbo-CAD-4 diffractometer | 1769 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 26.3°, θmin = 2.4° |
non–profiled ω scans | h = −10→10 |
Absorption correction: part of the refinement model (ΔF) (Walker & Stuart, 1983) | k = 0→9 |
Tmin = 0.968, Tmax = 0.986 | l = 0→21 |
2198 measured reflections | 3 standard reflections every 120 min |
2198 independent reflections | intensity decay: none |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.189 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0973P)2 + 0.6954P] where P = (Fo2 + 2Fc2)/3 |
2198 reflections | (Δ/σ)max = 0.001 |
157 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
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 | ||
H2' | −0.001 (6) | 0.484 (5) | 0.257 (2) | 0.084 (12)* | |
H1' | 0.171 (4) | 1.238 (4) | 0.2095 (19) | 0.059 (9)* | |
O2 | 0.0943 (2) | 0.4846 (2) | 0.23763 (11) | 0.0410 (5) | |
N3 | 0.0955 (2) | 0.6571 (3) | 0.21243 (12) | 0.0350 (5) | |
O1 | 0.2174 (2) | 1.1672 (2) | 0.18322 (12) | 0.0462 (5) | |
N2 | 0.1935 (2) | 0.9994 (2) | 0.21332 (12) | 0.0353 (5) | |
N1 | 0.3288 (3) | 0.9185 (3) | 0.11603 (11) | 0.0343 (5) | |
C2 | 0.1988 (3) | 0.7485 (3) | −0.00021 (14) | 0.0376 (6) | |
C9 | 0.2472 (3) | 0.8819 (3) | 0.17276 (13) | 0.0296 (5) | |
C10 | 0.2328 (3) | 0.6975 (3) | 0.19670 (13) | 0.0305 (5) | |
C1 | 0.3401 (3) | 0.8122 (3) | 0.05008 (12) | 0.0317 (5) | |
C6 | 0.4952 (3) | 0.7885 (3) | 0.03508 (14) | 0.0351 (5) | |
C11 | 0.3747 (3) | 0.5792 (3) | 0.20340 (18) | 0.0469 (7) | |
H11A | 0.3460 | 0.4633 | 0.2196 | 0.070* | |
H11B | 0.4669 | 0.6255 | 0.2422 | 0.070* | |
H11C | 0.4051 | 0.5706 | 0.1528 | 0.070* | |
C7 | 0.6462 (3) | 0.8467 (4) | 0.09158 (16) | 0.0452 (6) | |
H7A | 0.6159 | 0.9020 | 0.1366 | 0.068* | |
H7B | 0.7055 | 0.9305 | 0.0661 | 0.068* | |
H7C | 0.7159 | 0.7456 | 0.1090 | 0.068* | |
C3 | 0.2175 (4) | 0.6656 (4) | −0.06836 (16) | 0.0482 (7) | |
H3 | 0.1240 | 0.6211 | −0.1034 | 0.058* | |
C5 | 0.5062 (3) | 0.7056 (4) | −0.03430 (15) | 0.0444 (6) | |
H5 | 0.6101 | 0.6890 | −0.0463 | 0.053* | |
C4 | 0.3678 (4) | 0.6472 (4) | −0.08579 (15) | 0.0502 (7) | |
H4 | 0.3769 | 0.5942 | −0.1334 | 0.060* | |
C8 | 0.0302 (3) | 0.7682 (4) | 0.01495 (17) | 0.0509 (7) | |
H8A | 0.0368 | 0.8288 | 0.0646 | 0.076* | |
H8B | −0.0183 | 0.6528 | 0.0174 | 0.076* | |
H8C | −0.0376 | 0.8360 | −0.0272 | 0.076* | |
H1 | 0.341 (3) | 1.021 (4) | 0.1108 (16) | 0.037 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0473 (10) | 0.0298 (9) | 0.0525 (11) | −0.0013 (7) | 0.0253 (9) | 0.0042 (7) |
N3 | 0.0396 (11) | 0.0297 (10) | 0.0393 (11) | 0.0005 (8) | 0.0163 (9) | 0.0020 (8) |
O1 | 0.0620 (12) | 0.0279 (9) | 0.0553 (11) | 0.0036 (8) | 0.0271 (10) | 0.0000 (8) |
N2 | 0.0412 (11) | 0.0295 (11) | 0.0390 (11) | 0.0006 (8) | 0.0168 (9) | −0.0013 (8) |
N1 | 0.0464 (12) | 0.0267 (10) | 0.0351 (10) | −0.0032 (8) | 0.0202 (9) | −0.0018 (8) |
C2 | 0.0434 (13) | 0.0358 (13) | 0.0335 (12) | −0.0010 (10) | 0.0085 (10) | 0.0039 (10) |
C9 | 0.0295 (10) | 0.0303 (11) | 0.0304 (10) | 0.0001 (9) | 0.0097 (8) | −0.0009 (9) |
C10 | 0.0353 (11) | 0.0292 (11) | 0.0296 (11) | 0.0005 (9) | 0.0126 (9) | −0.0008 (9) |
C1 | 0.0422 (12) | 0.0280 (11) | 0.0276 (11) | 0.0024 (9) | 0.0135 (9) | 0.0021 (8) |
C6 | 0.0415 (13) | 0.0316 (12) | 0.0350 (12) | 0.0003 (10) | 0.0144 (10) | 0.0024 (9) |
C11 | 0.0436 (14) | 0.0385 (14) | 0.0650 (17) | 0.0095 (11) | 0.0257 (13) | 0.0155 (12) |
C7 | 0.0402 (14) | 0.0526 (16) | 0.0457 (14) | −0.0024 (11) | 0.0159 (11) | 0.0001 (12) |
C3 | 0.0588 (17) | 0.0460 (15) | 0.0367 (13) | −0.0038 (13) | 0.0039 (12) | −0.0034 (12) |
C5 | 0.0563 (16) | 0.0441 (15) | 0.0388 (13) | 0.0080 (12) | 0.0235 (12) | 0.0010 (11) |
C4 | 0.0727 (19) | 0.0463 (16) | 0.0343 (13) | 0.0043 (14) | 0.0176 (13) | −0.0069 (11) |
C8 | 0.0403 (14) | 0.0629 (19) | 0.0480 (15) | −0.0055 (13) | 0.0062 (12) | 0.0027 (13) |
O2—N3 | 1.396 (3) | C6—C7 | 1.498 (4) |
O2—H2' | 0.94 (5) | C11—H11A | 0.9800 |
N3—C10 | 1.282 (3) | C11—H11B | 0.9800 |
O1—N2 | 1.423 (3) | C11—H11C | 0.9800 |
O1—H1' | 0.86 (3) | C7—H7A | 0.9800 |
N2—C9 | 1.290 (3) | C7—H7B | 0.9800 |
N1—C9 | 1.358 (3) | C7—H7C | 0.9800 |
N1—C1 | 1.438 (3) | C3—C4 | 1.371 (4) |
N1—H1 | 0.80 (3) | C3—H3 | 0.9500 |
C2—C3 | 1.396 (4) | C5—C4 | 1.383 (4) |
C2—C1 | 1.404 (3) | C5—H5 | 0.9500 |
C2—C8 | 1.506 (4) | C4—H4 | 0.9500 |
C9—C10 | 1.489 (3) | C8—H8A | 0.9800 |
C10—C11 | 1.482 (3) | C8—H8B | 0.9800 |
C1—C6 | 1.398 (3) | C8—H8C | 0.9800 |
C6—C5 | 1.397 (3) | ||
N3—O2—H2' | 101 (3) | C10—C11—H11C | 109.5 |
C10—N3—O2 | 111.52 (19) | H11A—C11—H11C | 109.5 |
N2—O1—H1' | 105 (2) | H11B—C11—H11C | 109.5 |
C9—N2—O1 | 109.37 (18) | C6—C7—H7A | 109.5 |
C9—N1—C1 | 127.5 (2) | C6—C7—H7B | 109.5 |
C9—N1—H1 | 113 (2) | H7A—C7—H7B | 109.5 |
C1—N1—H1 | 115 (2) | C6—C7—H7C | 109.5 |
C3—C2—C1 | 117.5 (2) | H7A—C7—H7C | 109.5 |
C3—C2—C8 | 119.0 (2) | H7B—C7—H7C | 109.5 |
C1—C2—C8 | 123.5 (2) | C4—C3—C2 | 121.4 (3) |
N2—C9—N1 | 123.8 (2) | C4—C3—H3 | 119.3 |
N2—C9—C10 | 116.59 (19) | C2—C3—H3 | 119.3 |
N1—C9—C10 | 119.29 (19) | C4—C5—C6 | 120.8 (2) |
N3—C10—C11 | 125.6 (2) | C4—C5—H5 | 119.6 |
N3—C10—C9 | 115.0 (2) | C6—C5—H5 | 119.6 |
C11—C10—C9 | 119.4 (2) | C3—C4—C5 | 120.3 (2) |
C6—C1—C2 | 122.1 (2) | C3—C4—H4 | 119.9 |
C6—C1—N1 | 117.0 (2) | C5—C4—H4 | 119.9 |
C2—C1—N1 | 120.7 (2) | C2—C8—H8A | 109.5 |
C5—C6—C1 | 117.8 (2) | C2—C8—H8B | 109.5 |
C5—C6—C7 | 120.5 (2) | H8A—C8—H8B | 109.5 |
C1—C6—C7 | 121.7 (2) | C2—C8—H8C | 109.5 |
C10—C11—H11A | 109.5 | H8A—C8—H8C | 109.5 |
C10—C11—H11B | 109.5 | H8B—C8—H8C | 109.5 |
H11A—C11—H11B | 109.5 | ||
O1—N2—C9—N1 | 6.4 (3) | C8—C2—C1—N1 | −6.8 (4) |
O1—N2—C9—C10 | 179.61 (19) | C9—N1—C1—C6 | −132.5 (3) |
C1—N1—C9—N2 | −154.7 (2) | C9—N1—C1—C2 | 52.8 (3) |
C1—N1—C9—C10 | 32.3 (4) | C2—C1—C6—C5 | 3.0 (4) |
O2—N3—C10—C11 | 0.2 (3) | N1—C1—C6—C5 | −171.7 (2) |
O2—N3—C10—C9 | −177.37 (18) | C2—C1—C6—C7 | −175.9 (2) |
N2—C9—C10—N3 | 44.3 (3) | N1—C1—C6—C7 | 9.4 (3) |
N1—C9—C10—N3 | −142.2 (2) | C1—C2—C3—C4 | −0.1 (4) |
N2—C9—C10—C11 | −133.5 (2) | C8—C2—C3—C4 | 178.7 (3) |
N1—C9—C10—C11 | 40.0 (3) | C1—C6—C5—C4 | −0.7 (4) |
C3—C2—C1—C6 | −2.6 (3) | C7—C6—C5—C4 | 178.2 (2) |
C8—C2—C1—C6 | 178.7 (2) | C2—C3—C4—C5 | 2.3 (4) |
C3—C2—C1—N1 | 171.9 (2) | C6—C5—C4—C3 | −1.9 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1′···O2i | 0.86 (4) | 2.09 (4) | 2.889 (3) | 154 (3) |
O2—H2′···N2ii | 0.94 (3) | 1.81 (5) | 2.742 (3) | 174 (4) |
N1—H1···O1 | 0.80 (3) | 2.13 (3) | 2.53 (3) | 111 (3) |
Symmetry codes: (i) x, y−1, z; (ii) −x, y+1/2, −z+1/2. |
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