Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801008133/tk6012sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801008133/tk6012Isup2.hkl |
CCDC reference: 170306
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999a); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON (Spek, 1999).
C14H11N3O2 | Dx = 1.354 Mg m−3 |
Mr = 253.26 | Melting point: 493–495 K K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71069 Å |
a = 12.2039 (8) Å | Cell parameters from 25 reflections |
b = 12.2039 (8) Å | θ = 19.0–21.0° |
c = 8.343 (1) Å | µ = 0.09 mm−1 |
V = 1242.57 (19) Å3 | T = 298 K |
Z = 4 | Prism, colourless |
F(000) = 528 | 0.35 × 0.25 × 0.20 mm |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.000 |
Radiation source: X-ray tube | θmax = 25.0°, θmin = 2.4° |
Graphite monochromator | h = 0→14 |
ω–2θ scans | k = 0→14 |
1277 measured reflections | l = 0→9 |
1277 independent reflections | 3 standard reflections every 150 reflections |
655 reflections with I > 2σ(I) | intensity decay: 10.2% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.0361P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.102 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.16 e Å−3 |
1277 reflections | Δρmin = −0.17 e Å−3 |
176 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.019 (3) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983) |
Secondary atom site location: difference Fourier map |
Experimental. Although the a and b cell parameters were identical, no symmetry higher than orthorhombic could be identified. The poor data to parameter ratio (7.26) (non-centrosymmetric) arises because of the significant decomposition (ca 12%) in the crystal. Since there is no possibility of re-collection possibly at low temperature this less than desirable feature of the structure has to be accepted. |
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. Absolute configuration could not be determined with any certainty (Flack, 1983). A 10% intensity loss during the data collection period indicated significant crystal decay and was allowed for by a linear correction. |
x | y | z | Uiso*/Ueq | ||
O40 | 0.2233 (3) | 0.4828 (3) | 0.0420 (5) | 0.0838 (15) | |
O41 | 0.3489 (2) | 0.5638 (3) | 0.1892 (5) | 0.0650 (11) | |
N1 | 0.4301 (3) | 0.1840 (3) | −0.2118 (5) | 0.0459 (10) | |
N2 | 0.3396 (3) | 0.2311 (3) | −0.2740 (5) | 0.0546 (12) | |
N3 | 0.3145 (3) | 0.3163 (3) | −0.1863 (5) | 0.0459 (11) | |
C4 | 0.3989 (4) | 0.4014 (3) | 0.0608 (6) | 0.0406 (12) | |
C5 | 0.4878 (4) | 0.3900 (4) | 0.1578 (6) | 0.0544 (15) | |
C6 | 0.5647 (4) | 0.3056 (5) | 0.1386 (6) | 0.0674 (16) | |
C7 | 0.5544 (4) | 0.2277 (4) | 0.0208 (7) | 0.0554 (15) | |
C8 | 0.4643 (4) | 0.2399 (3) | −0.0791 (6) | 0.0403 (12) | |
C9 | 0.3888 (4) | 0.3245 (3) | −0.0626 (6) | 0.0367 (11) | |
C10 | 0.4714 (4) | 0.0825 (4) | −0.2818 (6) | 0.0576 (15) | |
C11 | 0.4051 (4) | −0.0147 (4) | −0.2357 (6) | 0.0510 (14) | |
C12 | 0.4401 (5) | −0.0872 (5) | −0.1215 (7) | 0.0642 (16) | |
C13 | 0.3794 (7) | −0.1784 (5) | −0.0795 (7) | 0.087 (2) | |
C14 | 0.2807 (7) | −0.1967 (6) | −0.1505 (11) | 0.097 (3) | |
C15 | 0.2418 (5) | −0.1251 (5) | −0.2628 (10) | 0.095 (2) | |
C16 | 0.3041 (5) | −0.0345 (4) | −0.3065 (8) | 0.0747 (19) | |
C41 | 0.3141 (4) | 0.4855 (4) | 0.0942 (6) | 0.0449 (13) | |
H41 | 0.285 (5) | 0.606 (5) | 0.223 (9) | 0.101* | |
H5 | 0.498 | 0.442 | 0.242 | 0.065* | |
H6 | 0.626 | 0.302 | 0.210 | 0.081* | |
H7 | 0.606 | 0.170 | 0.008 | 0.066* | |
H12 | 0.508 | −0.075 | −0.069 | 0.077* | |
H13 | 0.407 | −0.228 | −0.001 | 0.104* | |
H14 | 0.239 | −0.259 | −0.122 | 0.117* | |
H15 | 0.172 | −0.137 | −0.311 | 0.114* | |
H16 | 0.277 | 0.014 | −0.386 | 0.090* | |
H101 | 0.545 | 0.072 | −0.246 | 0.069* | |
H102 | 0.470 | 0.089 | −0.395 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O40 | 0.049 (3) | 0.076 (3) | 0.127 (4) | 0.023 (2) | −0.022 (3) | −0.045 (3) |
O41 | 0.0377 (19) | 0.063 (2) | 0.094 (3) | 0.0063 (19) | 0.001 (2) | −0.034 (2) |
N1 | 0.044 (2) | 0.039 (2) | 0.054 (3) | 0.008 (2) | 0.005 (2) | −0.006 (2) |
N2 | 0.050 (2) | 0.051 (2) | 0.064 (3) | 0.003 (2) | −0.008 (3) | −0.006 (2) |
N3 | 0.046 (3) | 0.034 (2) | 0.058 (3) | 0.007 (2) | −0.006 (3) | −0.002 (2) |
C4 | 0.035 (3) | 0.038 (3) | 0.049 (3) | 0.003 (2) | 0.004 (3) | −0.001 (3) |
C5 | 0.053 (3) | 0.054 (3) | 0.056 (4) | 0.009 (3) | 0.002 (3) | −0.015 (3) |
C6 | 0.057 (3) | 0.091 (4) | 0.054 (3) | 0.035 (4) | −0.016 (3) | −0.013 (4) |
C7 | 0.047 (3) | 0.063 (3) | 0.056 (3) | 0.023 (3) | −0.001 (3) | 0.004 (3) |
C8 | 0.042 (3) | 0.039 (3) | 0.040 (3) | 0.007 (2) | 0.009 (3) | 0.002 (2) |
C9 | 0.035 (3) | 0.034 (2) | 0.042 (3) | 0.002 (2) | −0.001 (3) | 0.004 (2) |
C10 | 0.062 (4) | 0.043 (3) | 0.068 (4) | 0.009 (3) | 0.012 (3) | −0.009 (3) |
C11 | 0.061 (4) | 0.036 (3) | 0.055 (4) | 0.006 (3) | 0.005 (3) | −0.008 (3) |
C12 | 0.078 (4) | 0.057 (3) | 0.058 (4) | 0.010 (4) | 0.002 (3) | −0.017 (3) |
C13 | 0.143 (7) | 0.059 (4) | 0.059 (4) | 0.011 (5) | 0.033 (5) | 0.002 (4) |
C14 | 0.128 (7) | 0.063 (4) | 0.100 (7) | −0.024 (5) | 0.045 (6) | −0.021 (4) |
C15 | 0.083 (5) | 0.086 (5) | 0.116 (7) | −0.027 (4) | −0.005 (5) | −0.034 (5) |
C16 | 0.074 (4) | 0.059 (4) | 0.091 (5) | −0.001 (3) | −0.011 (4) | −0.012 (4) |
C41 | 0.037 (3) | 0.035 (3) | 0.063 (4) | −0.002 (3) | −0.001 (3) | −0.007 (3) |
O40—C41 | 1.191 (5) | C7—H7 | 0.95 |
O41—C41 | 1.312 (5) | C8—C9 | 1.392 (6) |
O41—H41 | 0.98 (6) | C10—C11 | 1.486 (6) |
N1—N2 | 1.348 (5) | C10—H101 | 0.95 |
N1—C8 | 1.365 (5) | C10—H102 | 0.95 |
N1—C10 | 1.460 (5) | C11—C12 | 1.369 (7) |
N2—N3 | 1.307 (5) | C11—C16 | 1.388 (7) |
N3—C9 | 1.377 (5) | C12—C13 | 1.382 (8) |
C4—C5 | 1.361 (6) | C12—H12 | 0.95 |
C4—C9 | 1.398 (5) | C13—C14 | 1.361 (9) |
C4—C41 | 1.484 (6) | C13—H13 | 0.95 |
C5—C6 | 1.402 (6) | C14—C15 | 1.366 (9) |
C5—H5 | 0.95 | C14—H14 | 0.95 |
C6—C7 | 1.374 (6) | C15—C16 | 1.391 (8) |
C6—H6 | 0.95 | C15—H15 | 0.95 |
C7—C8 | 1.387 (6) | C16—H16 | 0.95 |
C41—O41—H41 | 107 (4) | C11—C10—H101 | 109 |
N2—N1—C8 | 110.5 (3) | N1—C10—H102 | 109 |
N2—N1—C10 | 119.4 (4) | C11—C10—H102 | 109 |
C8—N1—C10 | 130.0 (4) | H101—C10—H102 | 109 |
N3—N2—N1 | 108.4 (4) | C12—C11—C16 | 117.5 (5) |
N2—N3—C9 | 108.9 (4) | C12—C11—C10 | 121.8 (5) |
C5—C4—C9 | 116.1 (4) | C16—C11—C10 | 120.8 (5) |
C5—C4—C41 | 121.0 (4) | C11—C12—C13 | 122.0 (6) |
C9—C4—C41 | 122.7 (4) | C11—C12—H12 | 119 |
C4—C5—C6 | 122.7 (5) | C13—C12—H12 | 119 |
C4—C5—H5 | 119 | C14—C13—C12 | 119.8 (7) |
C6—C5—H5 | 119 | C14—C13—H13 | 120 |
C7—C6—C5 | 121.9 (5) | C12—C13—H13 | 120 |
C7—C6—H6 | 119 | C13—C14—C15 | 120.1 (7) |
C5—C6—H6 | 119 | C13—C14—H14 | 120 |
C6—C7—C8 | 115.4 (5) | C15—C14—H14 | 120 |
C6—C7—H7 | 122 | C14—C15—C16 | 119.9 (7) |
C8—C7—H7 | 122 | C14—C15—H15 | 120 |
N1—C8—C7 | 132.5 (4) | C16—C15—H15 | 120 |
N1—C8—C9 | 104.4 (4) | C11—C16—C15 | 120.8 (6) |
C7—C8—C9 | 123.0 (5) | C11—C16—H16 | 120 |
N3—C9—C8 | 107.9 (4) | C15—C16—H16 | 120 |
N3—C9—C4 | 131.2 (4) | O40—C41—O41 | 122.8 (5) |
C8—C9—C4 | 120.8 (4) | O40—C41—C4 | 124.1 (5) |
N1—C10—C11 | 112.7 (4) | O41—C41—C4 | 113.0 (4) |
N1—C10—H101 | 109 | ||
C8—N1—N2—N3 | 0.4 (5) | C41—C4—C9—N3 | 9.6 (7) |
C10—N1—N2—N3 | 176.1 (4) | C5—C4—C9—C8 | 2.2 (6) |
N1—N2—N3—C9 | −0.9 (5) | C41—C4—C9—C8 | −173.1 (4) |
C9—C4—C5—C6 | −1.0 (7) | N2—N1—C10—C11 | −75.9 (5) |
C41—C4—C5—C6 | 174.3 (5) | C8—N1—C10—C11 | 98.7 (5) |
C4—C5—C6—C7 | −0.7 (9) | N1—C10—C11—C12 | −102.9 (5) |
C5—C6—C7—C8 | 1.2 (8) | N1—C10—C11—C16 | 76.4 (6) |
N2—N1—C8—C7 | −176.3 (5) | C16—C11—C12—C13 | 1.4 (7) |
C10—N1—C8—C7 | 8.6 (8) | C10—C11—C12—C13 | −179.3 (5) |
N2—N1—C8—C9 | 0.3 (4) | C11—C12—C13—C14 | −1.3 (9) |
C10—N1—C8—C9 | −174.8 (4) | C12—C13—C14—C15 | −0.1 (10) |
C6—C7—C8—N1 | 176.0 (5) | C13—C14—C15—C16 | 1.1 (10) |
C6—C7—C8—C9 | −0.1 (7) | C12—C11—C16—C15 | −0.3 (8) |
N2—N3—C9—C8 | 1.1 (5) | C10—C11—C16—C15 | −179.6 (5) |
N2—N3—C9—C4 | 178.7 (4) | C14—C15—C16—C11 | −0.9 (10) |
N1—C8—C9—N3 | −0.8 (5) | C5—C4—C41—O40 | −160.2 (5) |
C7—C8—C9—N3 | 176.2 (4) | C9—C4—C41—O40 | 14.8 (8) |
N1—C8—C9—C4 | −178.7 (4) | C5—C4—C41—O41 | 19.2 (7) |
C7—C8—C9—C4 | −1.7 (7) | C9—C4—C41—O41 | −165.8 (4) |
C5—C4—C9—N3 | −175.2 (5) |