Supporting information
CCDC references: 166507; 169363; 169364
Data collection: Kuma KM4CCD Software; cell refinement: Kuma KM4CCD Software; data reduction: Kuma KM4CCD Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3; software used to prepare material for publication: SHELXL97.
C6H6N2O2 | Dx = 1.492 Mg m−3 |
Mr = 138.13 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 1415 reflections |
a = 18.873 (2) Å | θ = 3.4–28.2° |
b = 6.5212 (9) Å | µ = 0.12 mm−1 |
c = 4.9980 (7) Å | T = 110 K |
V = 615.13 (14) Å3 | Plate, yellow |
Z = 4 | 1.02 × 0.67 × 0.18 mm |
F(000) = 288 |
Kuma Diffraction KM4CCD diffractometer | 1305 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 29.6°, θmin = 3.1° |
ω scans | h = −26→25 |
4413 measured reflections | k = −9→8 |
1357 independent reflections | l = −6→5 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | Fixed |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.0638P)2 + 0.1839P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.108 | (Δ/σ)max = 0.001 |
S = 1.10 | Δρmax = 0.27 e Å−3 |
1357 reflections | Δρmin = −0.29 e Å−3 |
92 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.29 (2) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.5 (15) |
C6H6N2O2 | V = 615.13 (14) Å3 |
Mr = 138.13 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 18.873 (2) Å | µ = 0.12 mm−1 |
b = 6.5212 (9) Å | T = 110 K |
c = 4.9980 (7) Å | 1.02 × 0.67 × 0.18 mm |
Kuma Diffraction KM4CCD diffractometer | 1305 reflections with I > 2σ(I) |
4413 measured reflections | Rint = 0.025 |
1357 independent reflections |
R[F2 > 2σ(F2)] = 0.040 | Fixed |
wR(F2) = 0.108 | Δρmax = 0.27 e Å−3 |
S = 1.10 | Δρmin = −0.29 e Å−3 |
1357 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
92 parameters | Absolute structure parameter: −0.5 (15) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.14178 (7) | 0.57722 (19) | 0.2389 (3) | 0.0204 (3) | |
O1 | 0.10120 (7) | 0.43100 (18) | 0.2081 (3) | 0.0320 (3) | |
C1 | 0.12426 (8) | 0.7287 (2) | 0.4454 (3) | 0.0177 (3) | |
O2 | 0.19549 (6) | 0.60121 (19) | 0.1048 (3) | 0.0298 (3) | |
N2 | 0.19586 (7) | 1.21243 (19) | 0.7026 (3) | 0.0219 (3) | |
H2A | 0.2344 | 1.2261 | 0.6052 | 0.026* | |
H2B | 0.1854 | 1.3049 | 0.8246 | 0.026* | |
C2 | 0.16823 (8) | 0.8982 (2) | 0.4699 (3) | 0.0180 (3) | |
H2 | 0.2086 | 0.9140 | 0.3581 | 0.022* | |
C4 | 0.09147 (8) | 1.0157 (2) | 0.8234 (3) | 0.0212 (3) | |
H4 | 0.0796 | 1.1147 | 0.9555 | 0.025* | |
C3 | 0.15155 (8) | 1.0450 (2) | 0.6637 (3) | 0.0179 (3) | |
C6 | 0.06434 (8) | 0.6964 (2) | 0.5997 (4) | 0.0212 (3) | |
H6 | 0.0352 | 0.5791 | 0.5755 | 0.025* | |
C5 | 0.04893 (8) | 0.8435 (2) | 0.7910 (4) | 0.0228 (3) | |
H5 | 0.0085 | 0.8263 | 0.9021 | 0.027* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0227 (6) | 0.0186 (5) | 0.0201 (7) | 0.0011 (4) | −0.0027 (6) | −0.0046 (5) |
O1 | 0.0355 (6) | 0.0247 (5) | 0.0358 (8) | −0.0076 (5) | 0.0016 (6) | −0.0127 (6) |
C1 | 0.0193 (6) | 0.0176 (6) | 0.0161 (7) | 0.0022 (5) | −0.0029 (6) | −0.0043 (5) |
O2 | 0.0285 (6) | 0.0316 (6) | 0.0293 (8) | −0.0008 (5) | 0.0055 (6) | −0.0130 (5) |
N2 | 0.0227 (6) | 0.0200 (5) | 0.0230 (7) | −0.0014 (4) | −0.0005 (5) | −0.0074 (5) |
C2 | 0.0176 (6) | 0.0189 (6) | 0.0175 (7) | −0.0001 (5) | −0.0006 (6) | −0.0029 (5) |
C4 | 0.0210 (6) | 0.0232 (7) | 0.0195 (8) | 0.0036 (5) | −0.0007 (6) | −0.0052 (6) |
C3 | 0.0180 (6) | 0.0190 (6) | 0.0167 (8) | 0.0025 (5) | −0.0046 (5) | −0.0027 (5) |
C6 | 0.0200 (6) | 0.0216 (7) | 0.0220 (8) | −0.0014 (5) | −0.0013 (6) | −0.0023 (6) |
C5 | 0.0197 (6) | 0.0281 (7) | 0.0205 (8) | −0.0006 (5) | 0.0027 (6) | −0.0016 (6) |
N1—O2 | 1.2253 (19) | C2—C3 | 1.398 (2) |
N1—O1 | 1.2328 (16) | C2—H2 | 0.9500 |
N1—C1 | 1.4665 (19) | C4—C5 | 1.390 (2) |
C1—C6 | 1.385 (2) | C4—C3 | 1.400 (2) |
C1—C2 | 1.3874 (18) | C4—H4 | 0.9500 |
N2—C3 | 1.3892 (17) | C6—C5 | 1.385 (2) |
N2—H2A | 0.8800 | C6—H6 | 0.9500 |
N2—H2B | 0.8800 | C5—H5 | 0.9500 |
O2—N1—O1 | 122.99 (14) | C5—C4—C3 | 120.76 (14) |
O2—N1—C1 | 119.05 (12) | C5—C4—H4 | 119.6 |
O1—N1—C1 | 117.96 (13) | C3—C4—H4 | 119.6 |
C6—C1—C2 | 124.09 (13) | N2—C3—C2 | 119.98 (14) |
C6—C1—N1 | 118.26 (12) | N2—C3—C4 | 120.99 (14) |
C2—C1—N1 | 117.64 (13) | C2—C3—C4 | 118.98 (13) |
C3—N2—H2A | 120.0 | C1—C6—C5 | 116.77 (13) |
C3—N2—H2B | 120.0 | C1—C6—H6 | 121.6 |
H2A—N2—H2B | 120.0 | C5—C6—H6 | 121.6 |
C1—C2—C3 | 118.16 (14) | C6—C5—C4 | 121.24 (14) |
C1—C2—H2 | 120.9 | C6—C5—H5 | 119.4 |
C3—C2—H2 | 120.9 | C4—C5—H5 | 119.4 |
O2—N1—C1—C6 | −178.39 (15) | C1—C2—C3—C4 | −0.2 (2) |
O1—N1—C1—C6 | 1.9 (2) | C5—C4—C3—N2 | −177.33 (15) |
O2—N1—C1—C2 | 2.9 (2) | C5—C4—C3—C2 | 0.1 (2) |
O1—N1—C1—C2 | −176.83 (15) | C2—C1—C6—C5 | −0.8 (2) |
C6—C1—C2—C3 | 0.6 (2) | N1—C1—C6—C5 | −179.36 (15) |
N1—C1—C2—C3 | 179.18 (14) | C1—C6—C5—C4 | 0.6 (2) |
C1—C2—C3—N2 | 177.23 (14) | C3—C4—C5—C6 | −0.3 (3) |
Experimental details
Crystal data | |
Chemical formula | C6H6N2O2 |
Mr | 138.13 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 110 |
a, b, c (Å) | 18.873 (2), 6.5212 (9), 4.9980 (7) |
V (Å3) | 615.13 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 1.02 × 0.67 × 0.18 |
Data collection | |
Diffractometer | Kuma Diffraction KM4CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4413, 1357, 1305 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.694 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.108, 1.10 |
No. of reflections | 1357 |
No. of parameters | 92 |
No. of restraints | 1 |
H-atom treatment | Fixed |
Δρmax, Δρmin (e Å−3) | 0.27, −0.29 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | −0.5 (15) |
Computer programs: Kuma KM4CCD Software, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3, SHELXL97.