Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805024591/hk6034sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805024591/hk6034Isup2.hkl |
CCDC reference: 283935
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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).
C10H11N3O3 | Z = 2 |
Mr = 221.22 | F(000) = 232 |
Triclinic, P1 | Dx = 1.399 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.7940 (7) Å | Cell parameters from 7061 reflections |
b = 8.4531 (13) Å | θ = 2.7–27.9° |
c = 13.411 (2) Å | µ = 0.11 mm−1 |
α = 97.350 (12)° | T = 296 K |
β = 94.854 (12)° | Plate, colorless |
γ = 101.266 (12)° | 0.80 × 0.37 × 0.05 mm |
V = 525.25 (14) Å3 |
Stoe IPDS-II diffractometer | 2443 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1327 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.049 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.7°, θmin = 2.5° |
ω scans | h = −6→6 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −11→11 |
Tmin = 0.920, Tmax = 0.995 | l = −17→17 |
8616 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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0607P)2] where P = (Fo2 + 2Fc2)/3 |
2443 reflections | (Δ/σ)max < 0.001 |
178 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | 0.6727 (5) | 0.7623 (3) | 0.40810 (15) | 0.1142 (9) | |
O2 | 0.2956 (4) | 0.5922 (3) | 0.42843 (12) | 0.1031 (8) | |
O3 | 0.2278 (4) | 0.47209 (17) | 0.89320 (11) | 0.0773 (6) | |
N1 | 0.4909 (5) | 0.7079 (3) | 0.46004 (14) | 0.0760 (7) | |
N2 | 0.5574 (4) | 0.9718 (2) | 0.86513 (13) | 0.0683 (6) | |
N3 | 0.1970 (3) | 0.75853 (18) | 0.80550 (11) | 0.0543 (5) | |
C1 | 0.5115 (5) | 0.7834 (2) | 0.56586 (14) | 0.0594 (7) | |
C2 | 0.7353 (6) | 0.9169 (3) | 0.60125 (18) | 0.0706 (8) | |
C3 | 0.7654 (5) | 0.9889 (3) | 0.70051 (18) | 0.0697 (8) | |
C4 | 0.5711 (4) | 0.9250 (2) | 0.76324 (14) | 0.0561 (6) | |
C5 | 0.3478 (4) | 0.7912 (2) | 0.72494 (13) | 0.0505 (6) | |
C6 | 0.3109 (5) | 0.7164 (2) | 0.62499 (14) | 0.0560 (7) | |
C7 | 0.3337 (5) | 0.8703 (3) | 0.88552 (16) | 0.0631 (7) | |
C8 | −0.0468 (5) | 0.6251 (3) | 0.80638 (19) | 0.0638 (8) | |
C9 | 0.0397 (5) | 0.4632 (2) | 0.80549 (16) | 0.0620 (7) | |
C10 | 0.2970 (8) | 0.3200 (3) | 0.9038 (2) | 0.0878 (10) | |
H2 | 0.879 (6) | 0.960 (3) | 0.559 (2) | 0.0930* | |
H3 | 0.927 (6) | 1.086 (3) | 0.7256 (19) | 0.0930* | |
H6 | 0.165 (6) | 0.628 (3) | 0.600 (2) | 0.0930* | |
H7 | 0.268 (6) | 0.869 (3) | 0.952 (2) | 0.0930* | |
H8A | −0.177 (6) | 0.619 (3) | 0.745 (2) | 0.0930* | |
H8B | −0.130 (6) | 0.650 (3) | 0.870 (2) | 0.0930* | |
H9A | −0.135 (6) | 0.374 (3) | 0.8049 (19) | 0.0930* | |
H9B | 0.135 (6) | 0.431 (3) | 0.743 (2) | 0.0930* | |
H10A | 0.370 (7) | 0.277 (4) | 0.839 (3) | 0.1160* | |
H10B | 0.118 (7) | 0.235 (4) | 0.910 (2) | 0.1160* | |
H10C | 0.423 (7) | 0.331 (4) | 0.958 (3) | 0.1160* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1401 (18) | 0.1222 (16) | 0.0743 (12) | 0.0128 (14) | 0.0427 (13) | −0.0058 (11) |
O2 | 0.1071 (14) | 0.1233 (15) | 0.0573 (10) | 0.0054 (12) | −0.0080 (9) | −0.0277 (10) |
O3 | 0.0989 (12) | 0.0620 (9) | 0.0612 (9) | 0.0128 (8) | −0.0189 (8) | −0.0024 (6) |
N1 | 0.0912 (15) | 0.0837 (13) | 0.0510 (10) | 0.0264 (12) | 0.0014 (11) | −0.0064 (10) |
N2 | 0.0889 (14) | 0.0504 (9) | 0.0557 (10) | 0.0103 (9) | −0.0057 (9) | −0.0131 (7) |
N3 | 0.0608 (10) | 0.0510 (8) | 0.0480 (9) | 0.0167 (7) | −0.0031 (7) | −0.0057 (7) |
C1 | 0.0707 (14) | 0.0606 (11) | 0.0466 (11) | 0.0226 (10) | 0.0009 (10) | −0.0029 (9) |
C2 | 0.0801 (16) | 0.0619 (13) | 0.0686 (14) | 0.0130 (12) | 0.0120 (12) | 0.0053 (10) |
C3 | 0.0793 (15) | 0.0483 (11) | 0.0729 (14) | 0.0045 (10) | −0.0008 (12) | −0.0031 (10) |
C4 | 0.0691 (13) | 0.0432 (9) | 0.0516 (11) | 0.0166 (9) | −0.0080 (9) | −0.0067 (8) |
C5 | 0.0549 (11) | 0.0488 (10) | 0.0470 (10) | 0.0200 (8) | −0.0038 (8) | −0.0032 (8) |
C6 | 0.0553 (12) | 0.0558 (11) | 0.0520 (11) | 0.0168 (9) | −0.0093 (9) | −0.0077 (9) |
C7 | 0.0826 (16) | 0.0538 (11) | 0.0495 (11) | 0.0214 (11) | −0.0033 (10) | −0.0087 (9) |
C8 | 0.0574 (13) | 0.0701 (13) | 0.0601 (13) | 0.0167 (10) | 0.0024 (10) | −0.0066 (10) |
C9 | 0.0616 (13) | 0.0582 (12) | 0.0568 (12) | 0.0032 (10) | −0.0045 (10) | −0.0047 (9) |
C10 | 0.109 (2) | 0.0633 (15) | 0.0839 (18) | 0.0089 (14) | −0.0182 (16) | 0.0173 (13) |
O1—N1 | 1.218 (3) | C4—C5 | 1.405 (3) |
O2—N1 | 1.217 (3) | C5—C6 | 1.388 (3) |
O3—C9 | 1.405 (3) | C8—C9 | 1.505 (3) |
O3—C10 | 1.410 (3) | C2—H2 | 0.97 (3) |
N1—C1 | 1.467 (3) | C3—H3 | 1.01 (3) |
N2—C4 | 1.384 (3) | C6—H6 | 0.92 (3) |
N2—C7 | 1.308 (3) | C7—H7 | 0.97 (3) |
N3—C5 | 1.377 (2) | C8—H8A | 0.98 (3) |
N3—C7 | 1.361 (3) | C8—H8B | 0.99 (3) |
N3—C8 | 1.459 (3) | C9—H9A | 1.01 (3) |
C1—C2 | 1.398 (3) | C9—H9B | 1.02 (3) |
C1—C6 | 1.380 (3) | C10—H10A | 1.02 (4) |
C2—C3 | 1.375 (3) | C10—H10B | 1.02 (3) |
C3—C4 | 1.385 (3) | C10—H10C | 0.89 (4) |
O2···C9i | 3.335 (3) | C4···H8Aviii | 3.05 (3) |
O3···C7 | 3.321 (3) | C5···H9B | 3.06 (3) |
O3···N3 | 2.847 (2) | C5···H8Aviii | 2.95 (3) |
O1···H2 | 2.45 (3) | C6···H8A | 2.99 (3) |
O1···H9Bii | 2.77 (3) | C6···H9B | 3.07 (3) |
O1···H2iii | 2.82 (3) | C8···H6 | 3.03 (3) |
O2···H6 | 2.43 (3) | C10···H3x | 3.08 (3) |
O2···H9Bi | 2.92 (3) | H2···O1 | 2.45 (3) |
O2···H6i | 2.56 (3) | H2···O1iii | 2.82 (3) |
O2···H8Ai | 2.69 (3) | H2···H2iii | 2.14 (4) |
O3···H10Civ | 2.66 (4) | H3···C10xi | 3.08 (3) |
N2···N3 | 2.248 (2) | H6···O2 | 2.43 (3) |
N2···C10v | 3.413 (4) | H6···C8 | 3.03 (3) |
N2···C7vi | 3.395 (3) | H6···O2i | 2.56 (3) |
N3···O3 | 2.847 (2) | H7···H8B | 2.45 (4) |
N3···C3vii | 3.441 (3) | H7···N2vi | 2.63 (3) |
N3···N2 | 2.248 (2) | H8A···C4vii | 3.05 (3) |
N2···H10Av | 2.94 (3) | H8A···C5vii | 2.95 (3) |
N2···H7vi | 2.63 (3) | H8A···C6 | 2.99 (3) |
C2···C6viii | 3.522 (4) | H8A···O2i | 2.69 (3) |
C3···N3viii | 3.441 (3) | H8B···H7 | 2.45 (4) |
C3···C5viii | 3.536 (3) | H9A···H10Avii | 2.46 (4) |
C4···C8viii | 3.482 (3) | H9A···H10B | 2.35 (4) |
C5···C3vii | 3.536 (3) | H9B···C5 | 3.06 (3) |
C6···C9 | 3.592 (3) | H9B···C6 | 3.07 (3) |
C6···C2vii | 3.522 (4) | H9B···H10A | 2.32 (4) |
C7···C7vi | 3.586 (3) | H9B···O1ii | 2.77 (3) |
C7···N2vi | 3.395 (3) | H9B···O2i | 2.92 (3) |
C7···O3 | 3.321 (3) | H10A···N2ix | 2.94 (3) |
C8···C4vii | 3.482 (3) | H10A···H9Aviii | 2.46 (4) |
C9···O2i | 3.335 (3) | H10A···H9B | 2.32 (4) |
C9···C6 | 3.592 (3) | H10B···H9A | 2.35 (4) |
C10···N2ix | 3.413 (4) | H10C···O3iv | 2.66 (4) |
C9—O3—C10 | 111.92 (17) | C3—C2—H2 | 117.3 (16) |
O1—N1—O2 | 122.9 (2) | C2—C3—H3 | 119.6 (15) |
O1—N1—C1 | 118.5 (2) | C4—C3—H3 | 122.1 (15) |
O2—N1—C1 | 118.6 (2) | C1—C6—H6 | 122.4 (17) |
C4—N2—C7 | 104.01 (17) | C5—C6—H6 | 122.8 (17) |
C5—N3—C7 | 105.68 (16) | N2—C7—H7 | 124.7 (16) |
C5—N3—C8 | 127.05 (16) | N3—C7—H7 | 120.6 (16) |
C7—N3—C8 | 127.16 (18) | N3—C8—H8A | 107.5 (16) |
N1—C1—C2 | 118.2 (2) | N3—C8—H8B | 106.4 (16) |
N1—C1—C6 | 117.88 (18) | C9—C8—H8A | 108.1 (15) |
C2—C1—C6 | 123.94 (19) | C9—C8—H8B | 108.4 (15) |
C1—C2—C3 | 119.9 (2) | H8A—C8—H8B | 114 (2) |
C2—C3—C4 | 118.3 (2) | O3—C9—H9A | 109.7 (15) |
N2—C4—C3 | 129.77 (18) | O3—C9—H9B | 109.8 (16) |
N2—C4—C5 | 110.04 (16) | C8—C9—H9A | 110.0 (16) |
C3—C4—C5 | 120.20 (18) | C8—C9—H9B | 113.0 (15) |
N3—C5—C4 | 105.54 (15) | H9A—C9—H9B | 106 (2) |
N3—C5—C6 | 131.64 (17) | O3—C10—H10A | 109 (2) |
C4—C5—C6 | 122.82 (17) | O3—C10—H10B | 111 (2) |
C1—C6—C5 | 114.78 (18) | O3—C10—H10C | 110 (2) |
N2—C7—N3 | 114.74 (19) | H10A—C10—H10B | 105 (3) |
N3—C8—C9 | 112.40 (19) | H10A—C10—H10C | 113 (3) |
O3—C9—C8 | 108.13 (17) | H10B—C10—H10C | 110 (3) |
C1—C2—H2 | 122.7 (16) | ||
C10—O3—C9—C8 | 173.9 (2) | C5—N3—C8—C9 | 73.6 (3) |
O1—N1—C1—C6 | −177.4 (2) | C2—C1—C6—C5 | −0.5 (3) |
O2—N1—C1—C2 | −179.6 (2) | N1—C1—C2—C3 | −178.7 (2) |
O1—N1—C1—C2 | 1.5 (3) | N1—C1—C6—C5 | 178.36 (19) |
O2—N1—C1—C6 | 1.5 (3) | C6—C1—C2—C3 | 0.2 (4) |
C7—N2—C4—C3 | −179.8 (2) | C1—C2—C3—C4 | 0.5 (4) |
C4—N2—C7—N3 | 0.3 (3) | C2—C3—C4—C5 | −0.8 (3) |
C7—N2—C4—C5 | −0.5 (2) | C2—C3—C4—N2 | 178.5 (2) |
C7—N3—C5—C6 | 179.1 (2) | C3—C4—C5—C6 | 0.5 (3) |
C7—N3—C8—C9 | −101.9 (2) | C3—C4—C5—N3 | 179.86 (18) |
C5—N3—C7—N2 | −0.1 (3) | N2—C4—C5—C6 | −178.92 (18) |
C8—N3—C5—C6 | 2.7 (3) | N2—C4—C5—N3 | 0.4 (2) |
C7—N3—C5—C4 | −0.2 (2) | N3—C5—C6—C1 | −179.01 (19) |
C8—N3—C5—C4 | −176.54 (18) | C4—C5—C6—C1 | 0.2 (3) |
C8—N3—C7—N2 | 176.3 (2) | N3—C8—C9—O3 | 61.2 (2) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+2, −z+1; (iv) −x+1, −y+1, −z+2; (v) x, y+1, z; (vi) −x+1, −y+2, −z+2; (vii) x−1, y, z; (viii) x+1, y, z; (ix) x, y−1, z; (x) x−1, y−1, z; (xi) x+1, y+1, z. |