Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010038/ac2012sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010038/ac2012Isup2.hkl |
CCDC reference: 605227
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS90 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
C7H10N2O2 | F(000) = 328 |
Mr = 154.17 | Dx = 1.378 Mg m−3 |
Monoclinic, P21/c | Melting point = 43–44 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.1040 (8) Å | Cell parameters from 5362 reflections |
b = 15.2244 (18) Å | θ = 2.7–28.0° |
c = 7.4511 (9) Å | µ = 0.10 mm−1 |
β = 112.797 (2)° | T = 100 K |
V = 742.92 (15) Å3 | Plate, colorless |
Z = 4 | 0.37 × 0.29 × 0.09 mm |
Bruker SMART APEX diffractometer | 1728 independent reflections |
Radiation source: fine-focus sealed tube | 1636 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.013 |
Detector resolution: no pixels mm-1 | θmax = 28.0°, θmin = 3.1° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | k = −19→19 |
Tmin = 0.960, Tmax = 0.988 | l = −9→9 |
6360 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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.068 | All H-atom parameters refined |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0213P)2 + 0.3603P] where P = (Fo2 + 2Fc2)/3 |
1728 reflections | (Δ/σ)max = 0.001 |
140 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Experimental. Data were collected with a Bruker SMART APEX CCD-based diffractometer using /w-scans of width 0.3 °. and 30 s duration at a crystal-to-detector distance of 4.908 cm. Intensity decay over the course of the data collection was evaluated by recollecting the first 50 frames of data at the end of the experiment. No significant decay was noted. |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.25020 (11) | 0.57084 (4) | 0.39888 (9) | 0.01830 (16) | |
O2 | 0.23052 (11) | 0.46091 (5) | 0.59352 (10) | 0.02000 (17) | |
N1 | 0.24441 (12) | 0.45189 (5) | 0.11144 (11) | 0.01505 (17) | |
N2 | 0.19787 (12) | 0.34172 (5) | 0.28830 (12) | 0.01794 (18) | |
C1 | 0.22529 (13) | 0.42764 (6) | 0.28103 (13) | 0.01515 (19) | |
C2 | 0.20018 (15) | 0.30936 (7) | 0.11812 (14) | 0.0192 (2) | |
H2 | 0.1833 (19) | 0.2486 (9) | 0.0843 (18) | 0.022 (3)* | |
C3 | 0.22843 (14) | 0.37615 (7) | 0.00771 (14) | 0.0180 (2) | |
H3 | 0.2360 (19) | 0.3774 (8) | −0.1166 (19) | 0.022 (3)* | |
C4 | 0.27853 (15) | 0.53886 (6) | 0.04420 (14) | 0.0173 (2) | |
H4A | 0.1699 (19) | 0.5784 (8) | 0.0380 (17) | 0.020 (3)* | |
H4B | 0.4083 (19) | 0.5623 (8) | 0.1334 (18) | 0.019 (3)* | |
H4C | 0.2773 (19) | 0.5313 (8) | −0.0873 (19) | 0.023 (3)* | |
C5 | 0.23488 (13) | 0.48678 (6) | 0.44178 (13) | 0.01523 (19) | |
C6 | 0.25898 (15) | 0.63570 (6) | 0.54630 (14) | 0.0177 (2) | |
H6A | 0.3709 (18) | 0.6192 (7) | 0.6676 (17) | 0.015 (3)* | |
H6B | 0.1307 (18) | 0.6334 (8) | 0.5636 (17) | 0.017 (3)* | |
C7 | 0.29400 (17) | 0.72322 (7) | 0.46991 (15) | 0.0217 (2) | |
H7A | 0.304 (2) | 0.7695 (10) | 0.567 (2) | 0.036 (4)* | |
H7B | 0.179 (2) | 0.7379 (9) | 0.347 (2) | 0.028 (3)* | |
H7C | 0.421 (2) | 0.7219 (8) | 0.4487 (19) | 0.027 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0256 (4) | 0.0166 (3) | 0.0149 (3) | −0.0012 (3) | 0.0102 (3) | −0.0018 (3) |
O2 | 0.0254 (4) | 0.0216 (4) | 0.0146 (3) | −0.0001 (3) | 0.0095 (3) | 0.0010 (3) |
N1 | 0.0156 (4) | 0.0169 (4) | 0.0131 (4) | 0.0002 (3) | 0.0059 (3) | 0.0001 (3) |
N2 | 0.0186 (4) | 0.0174 (4) | 0.0181 (4) | −0.0004 (3) | 0.0074 (3) | 0.0000 (3) |
C1 | 0.0145 (4) | 0.0179 (4) | 0.0132 (4) | 0.0004 (3) | 0.0056 (3) | 0.0014 (3) |
C2 | 0.0193 (4) | 0.0182 (5) | 0.0200 (5) | −0.0008 (4) | 0.0077 (4) | −0.0032 (4) |
C3 | 0.0177 (4) | 0.0206 (5) | 0.0160 (4) | 0.0000 (4) | 0.0069 (4) | −0.0030 (4) |
C4 | 0.0200 (5) | 0.0175 (5) | 0.0157 (4) | −0.0002 (4) | 0.0084 (4) | 0.0020 (3) |
C5 | 0.0122 (4) | 0.0186 (5) | 0.0145 (4) | 0.0003 (3) | 0.0046 (3) | 0.0000 (3) |
C6 | 0.0214 (5) | 0.0179 (5) | 0.0152 (4) | 0.0003 (4) | 0.0089 (4) | −0.0027 (4) |
C7 | 0.0276 (5) | 0.0183 (5) | 0.0211 (5) | 0.0006 (4) | 0.0116 (4) | −0.0002 (4) |
O1—C5 | 1.3338 (12) | C3—H3 | 0.948 (13) |
O1—C6 | 1.4604 (11) | C4—H4A | 0.966 (12) |
O2—C5 | 1.2089 (12) | C4—H4B | 0.972 (12) |
N1—C3 | 1.3682 (12) | C4—H4C | 0.983 (13) |
N1—C1 | 1.3728 (12) | C6—C7 | 1.5070 (14) |
N1—C4 | 1.4686 (12) | C6—H6A | 0.977 (12) |
N2—C1 | 1.3266 (12) | C6—H6B | 0.969 (12) |
N2—C2 | 1.3664 (13) | C7—H7A | 0.991 (15) |
C1—C5 | 1.4787 (13) | C7—H7B | 0.988 (14) |
C2—C3 | 1.3707 (14) | C7—H7C | 0.974 (13) |
C2—H2 | 0.954 (13) | ||
C5—O1—C6 | 116.89 (7) | H4A—C4—H4C | 109.1 (10) |
C3—N1—C1 | 106.09 (8) | H4B—C4—H4C | 111.4 (10) |
C3—N1—C4 | 123.76 (8) | O2—C5—O1 | 124.81 (9) |
C1—N1—C4 | 130.15 (8) | O2—C5—C1 | 123.32 (9) |
C1—N2—C2 | 105.24 (8) | O1—C5—C1 | 111.87 (8) |
N2—C1—N1 | 111.79 (8) | O1—C6—C7 | 106.20 (8) |
N2—C1—C5 | 121.92 (8) | O1—C6—H6A | 107.7 (7) |
N1—C1—C5 | 126.29 (8) | C7—C6—H6A | 112.5 (7) |
N2—C2—C3 | 110.28 (9) | O1—C6—H6B | 107.9 (7) |
N2—C2—H2 | 123.3 (8) | C7—C6—H6B | 112.5 (7) |
C3—C2—H2 | 126.4 (8) | H6A—C6—H6B | 109.7 (10) |
N1—C3—C2 | 106.59 (8) | C6—C7—H7A | 109.2 (8) |
N1—C3—H3 | 120.7 (8) | C6—C7—H7B | 110.7 (8) |
C2—C3—H3 | 132.7 (8) | H7A—C7—H7B | 108.2 (11) |
N1—C4—H4A | 110.1 (7) | C6—C7—H7C | 109.9 (8) |
N1—C4—H4B | 109.7 (7) | H7A—C7—H7C | 109.0 (11) |
H4A—C4—H4B | 109.4 (10) | H7B—C7—H7C | 109.7 (11) |
N1—C4—H4C | 107.2 (7) | ||
C2—N2—C1—N1 | 0.25 (10) | N2—C2—C3—N1 | 0.09 (11) |
C2—N2—C1—C5 | −179.19 (8) | C6—O1—C5—O2 | −1.01 (13) |
C3—N1—C1—N2 | −0.20 (10) | C6—O1—C5—C1 | 179.45 (7) |
C4—N1—C1—N2 | −179.26 (9) | N2—C1—C5—O2 | 4.43 (14) |
C3—N1—C1—C5 | 179.20 (8) | N1—C1—C5—O2 | −174.91 (9) |
C4—N1—C1—C5 | 0.14 (15) | N2—C1—C5—O1 | −176.02 (8) |
C1—N2—C2—C3 | −0.20 (11) | N1—C1—C5—O1 | 4.63 (13) |
C1—N1—C3—C2 | 0.06 (10) | C5—O1—C6—C7 | 175.23 (8) |
C4—N1—C3—C2 | 179.20 (8) |