Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600576715004161/fs5100sup1.cif | |
Portable Document Format (PDF) file https://doi.org/10.1107/S1600576715004161/fs5100sup2.pdf | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600576715004161/fs5100Isup3.hkl |
CCDC references: 1013040; 1051528
Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); 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).
C7H10N2O2 | F(000) = 656 |
Mr = 154.17 | Dx = 1.226 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.822 (12) Å | Cell parameters from 90 reflections |
b = 4.850 (3) Å | θ = 5–15° |
c = 19.783 (14) Å | µ = 0.09 mm−1 |
β = 102.370 (9)° | T = 293 K |
V = 1670 (2) Å3 | Needle, colorless |
Z = 8 | 0.20 × 0.09 × 0.06 mm |
APEX II diffractometer | 1461 independent reflections |
Radiation source: fine-focus sealed tube | 871 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.075 |
OMEGA SCAN scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: empirical (using intensity measurements) software bruker | h = −21→21 |
Tmin = 0.552, Tmax = 0.746 | k = −5→5 |
8010 measured reflections | l = −23→23 |
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)] = 0.074 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.228 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0758P)2 + 6.8758P] where P = (Fo2 + 2Fc2)/3 |
1461 reflections | (Δ/σ)max < 0.001 |
100 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C7H10N2O2 | V = 1670 (2) Å3 |
Mr = 154.17 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 17.822 (12) Å | µ = 0.09 mm−1 |
b = 4.850 (3) Å | T = 293 K |
c = 19.783 (14) Å | 0.20 × 0.09 × 0.06 mm |
β = 102.370 (9)° |
APEX II diffractometer | 1461 independent reflections |
Absorption correction: empirical (using intensity measurements) software bruker | 871 reflections with I > 2σ(I) |
Tmin = 0.552, Tmax = 0.746 | Rint = 0.075 |
8010 measured reflections |
R[F2 > 2σ(F2)] = 0.074 | 0 restraints |
wR(F2) = 0.228 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.24 e Å−3 |
1461 reflections | Δρmin = −0.19 e Å−3 |
100 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | ||
C1 | 0.1212 (3) | 0.3506 (9) | −0.0069 (2) | 0.0514 (11) | |
C2 | 0.1700 (2) | 0.1805 (8) | 0.1933 (2) | 0.0475 (11) | |
C3 | 0.2245 (3) | 0.2668 (10) | 0.0929 (2) | 0.0546 (12) | |
H3A | 0.2521 | 0.4174 | 0.0770 | 0.066* | |
H3B | 0.2606 | 0.1171 | 0.1069 | 0.066* | |
C4 | 0.0588 (3) | 0.2240 (10) | −0.0579 (2) | 0.0621 (13) | |
H4 | 0.0581 | 0.0330 | −0.0621 | 0.075* | |
C5 | 0.0052 (3) | 0.3612 (12) | −0.0967 (3) | 0.0781 (16) | |
H5A | 0.0044 | 0.5525 | −0.0936 | 0.094* | |
H5B | −0.0330 | 0.2699 | −0.1281 | 0.094* | |
C6 | 0.1402 (3) | 0.3040 (10) | 0.2498 (2) | 0.0596 (13) | |
H6 | 0.1441 | 0.4941 | 0.2558 | 0.071* | |
C7 | 0.1092 (4) | 0.1646 (12) | 0.2913 (3) | 0.101 (2) | |
H7A | 0.1045 | −0.0258 | 0.2864 | 0.121* | |
H7B | 0.0911 | 0.2533 | 0.3263 | 0.121* | |
N1 | 0.1650 (2) | 0.1751 (7) | 0.03660 (17) | 0.0550 (10) | |
H1 | 0.1572 | 0.0010 | 0.0306 | 0.066* | |
N2 | 0.1961 (2) | 0.3576 (7) | 0.15207 (17) | 0.0505 (10) | |
H2 | 0.1960 | 0.5310 | 0.1611 | 0.061* | |
O1 | 0.1329 (2) | 0.6015 (6) | −0.00422 (18) | 0.0701 (11) | |
O2 | 0.17040 (19) | −0.0707 (6) | 0.18383 (17) | 0.0639 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.068 (3) | 0.040 (2) | 0.049 (2) | 0.006 (2) | 0.017 (2) | −0.001 (2) |
C2 | 0.055 (3) | 0.037 (2) | 0.047 (2) | 0.0042 (19) | 0.003 (2) | 0.0022 (19) |
C3 | 0.066 (3) | 0.048 (3) | 0.050 (3) | 0.004 (2) | 0.013 (2) | 0.003 (2) |
C4 | 0.091 (4) | 0.045 (3) | 0.048 (3) | 0.002 (3) | 0.011 (3) | −0.008 (2) |
C5 | 0.082 (4) | 0.067 (3) | 0.080 (4) | −0.007 (3) | 0.006 (3) | −0.002 (3) |
C6 | 0.081 (3) | 0.046 (3) | 0.055 (3) | 0.006 (2) | 0.022 (3) | −0.001 (2) |
C7 | 0.145 (6) | 0.067 (4) | 0.117 (5) | 0.016 (4) | 0.085 (5) | 0.013 (4) |
N1 | 0.083 (3) | 0.039 (2) | 0.042 (2) | −0.0007 (19) | 0.0122 (19) | −0.0014 (16) |
N2 | 0.071 (3) | 0.0359 (19) | 0.044 (2) | −0.0018 (17) | 0.0110 (18) | −0.0036 (16) |
O1 | 0.090 (3) | 0.0323 (17) | 0.083 (2) | −0.0001 (16) | 0.0084 (19) | 0.0018 (16) |
O2 | 0.091 (3) | 0.0319 (17) | 0.073 (2) | 0.0025 (15) | 0.0249 (19) | −0.0025 (15) |
C1—O1 | 1.234 (5) | C4—C5 | 1.277 (7) |
C1—N1 | 1.336 (5) | C4—H4 | 0.9300 |
C1—C4 | 1.467 (7) | C5—H5A | 0.9300 |
C2—O2 | 1.233 (5) | C5—H5B | 0.9300 |
C2—N2 | 1.334 (5) | C6—C7 | 1.277 (7) |
C2—C6 | 1.466 (6) | C6—H6 | 0.9300 |
C3—N1 | 1.435 (6) | C7—H7A | 0.9300 |
C3—N2 | 1.439 (5) | C7—H7B | 0.9300 |
C3—H3A | 0.9700 | N1—H1 | 0.8600 |
C3—H3B | 0.9700 | N2—H2 | 0.8600 |
O1—C1—N1 | 122.0 (4) | C4—C5—H5A | 120.0 |
O1—C1—C4 | 122.6 (4) | C4—C5—H5B | 120.0 |
N1—C1—C4 | 115.4 (4) | H5A—C5—H5B | 120.0 |
O2—C2—N2 | 122.0 (4) | C7—C6—C2 | 123.5 (5) |
O2—C2—C6 | 122.3 (4) | C7—C6—H6 | 118.3 |
N2—C2—C6 | 115.7 (4) | C2—C6—H6 | 118.3 |
N1—C3—N2 | 113.3 (4) | C6—C7—H7A | 120.0 |
N1—C3—H3A | 108.9 | C6—C7—H7B | 120.0 |
N2—C3—H3A | 108.9 | H7A—C7—H7B | 120.0 |
N1—C3—H3B | 108.9 | C1—N1—C3 | 122.4 (4) |
N2—C3—H3B | 108.9 | C1—N1—H1 | 118.8 |
H3A—C3—H3B | 107.7 | C3—N1—H1 | 118.8 |
C5—C4—C1 | 123.7 (5) | C2—N2—C3 | 121.9 (4) |
C5—C4—H4 | 118.1 | C2—N2—H2 | 119.0 |
C1—C4—H4 | 118.1 | C3—N2—H2 | 119.0 |
Experimental details
Crystal data | |
Chemical formula | C7H10N2O2 |
Mr | 154.17 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 17.822 (12), 4.850 (3), 19.783 (14) |
β (°) | 102.370 (9) |
V (Å3) | 1670 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.20 × 0.09 × 0.06 |
Data collection | |
Diffractometer | APEX II diffractometer |
Absorption correction | Empirical (using intensity measurements) software bruker |
Tmin, Tmax | 0.552, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8010, 1461, 871 |
Rint | 0.075 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.074, 0.228, 0.99 |
No. of reflections | 1461 |
No. of parameters | 100 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.19 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).