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
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.008 Å
- R factor = 0.042
- wR factor = 0.102
- Data-to-parameter ratio = 7.3
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level B:
SYMMS_02 Alert B The unit-cell lengths a and b should not be equal for an orthorhombic cell Cell 12.2039 12.2039 8.3430 Angles 90.0000 90.0000 90.0000
Author response: This fact was recognized and a comment made in exptl_special_details that our checks for higher symmetry indicated that the cell was orthorhombic (space group P21 21 21) not tetragonal. |
General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 24.97 From the CIF: _reflns_number_total 1277 Count of symmetry unique reflns 1277 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check
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) |