Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768102015033/ns0009sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768102015033/ns0009100sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768102015033/ns0009130sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768102015033/ns0009160sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768102015033/ns0009200sup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768102015033/ns0009300sup6.hkl |
CCDC references: 201615; 201616; 201617; 201618; 201619
Data collection: KUMA KM4CCD software, 1999 for 100; KUMA Diffraction Km4CCD software, 1999 for 130; KUMA Diffraction KM4CCD software, 1999 for 160, 200, 300. Cell refinement: KUMA KM4CCD software, 1999 for 100; KUMA Diffraction Km4CCD software, 1999 for 130; KUMA Diffraction KM4CCD software, 1999 for 160, 200, 300. Data reduction: KUMA KM4CCD software, 1999 for 100; KUMA Diffraction Km4CCD software, 1999 for 130; KUMA Diffraction KM4CCD software, 1999 for 160, 200, 300. Program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) for 100; SHELXS97 (Sheldrick, 1990) for 130, 160, 200, 300. For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEP-3 (Farrugia, 1997) for 100, 160, 200, 300; ORTEP-3 (Farrugia,1997) for 130. Software used to prepare material for publication: SHELXL97 (SHeldrick, 1997) for 100; SHELXL97 (Sheldrick, 1997) for 130, 160, 200, 300.
C6H4N2O4 | Dx = 1.643 Mg m−3 |
Mr = 168.11 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 1717 reflections |
a = 14.024 (2) Å | θ = 3.4–22.6° |
b = 13.182 (2) Å | µ = 0.14 mm−1 |
c = 3.677 (1) Å | T = 100 K |
V = 679.7 (2) Å3 | Prism, colourless |
Z = 4 | 0.72 × 0.33 × 0.23 mm |
F(000) = 344 |
KUMA Diffraction KM4CCD diffractometer | 1388 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.069 |
Graphite monochromator | θmax = 31.2°, θmin = 3.3° |
ω scan | h = −20→20 |
5634 measured reflections | k = −19→18 |
1448 independent reflections | l = −5→3 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.123 | Calculated w = 1/[σ2(Fo2) + (0.0769P)2 + 0.0678P] where P = (Fo2 + 2Fc2)/3 |
S = 1.16 | (Δ/σ)max < 0.001 |
1448 reflections | Δρmax = 0.28 e Å−3 |
109 parameters | Δρmin = −0.32 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.7 (14) |
C6H4N2O4 | V = 679.7 (2) Å3 |
Mr = 168.11 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 14.024 (2) Å | µ = 0.14 mm−1 |
b = 13.182 (2) Å | T = 100 K |
c = 3.677 (1) Å | 0.72 × 0.33 × 0.23 mm |
KUMA Diffraction KM4CCD diffractometer | 1388 reflections with I > 2σ(I) |
5634 measured reflections | Rint = 0.069 |
1448 independent reflections |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.123 | Δρmax = 0.28 e Å−3 |
S = 1.16 | Δρmin = −0.32 e Å−3 |
1448 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
109 parameters | Absolute structure parameter: −0.7 (14) |
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 | ||
C1 | 0.13529 (10) | 0.63651 (11) | 0.0893 (5) | 0.0160 (3) | |
C2 | 0.05064 (10) | 0.67924 (12) | −0.0312 (5) | 0.0163 (3) | |
H2 | 0.0012 | 0.6402 | −0.1254 | 0.020* | |
C3 | 0.04439 (10) | 0.78380 (12) | −0.0025 (5) | 0.0176 (3) | |
C4 | 0.11756 (12) | 0.84440 (11) | 0.1306 (6) | 0.0206 (3) | |
H4 | 0.1104 | 0.9144 | 0.1463 | 0.025* | |
C5 | 0.20157 (11) | 0.79778 (12) | 0.2396 (6) | 0.0207 (3) | |
H5 | 0.2521 | 0.8371 | 0.3233 | 0.025* | |
C6 | 0.21083 (10) | 0.69298 (12) | 0.2247 (5) | 0.0190 (3) | |
H46 | 0.2664 | 0.6614 | 0.3037 | 0.023* | |
N1 | 0.14534 (10) | 0.52547 (10) | 0.0758 (5) | 0.0205 (3) | |
N2 | −0.04511 (10) | 0.83199 (12) | −0.1209 (5) | 0.0227 (3) | |
O1 | 0.21261 (10) | 0.48722 (10) | 0.2385 (6) | 0.0343 (4) | |
O2 | 0.08674 (10) | 0.47695 (10) | −0.0975 (5) | 0.0305 (4) | |
O3 | −0.10001 (9) | 0.78134 (12) | −0.3058 (5) | 0.0316 (4) | |
O4 | −0.06021 (10) | 0.91926 (10) | −0.0261 (6) | 0.0374 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0168 (6) | 0.0165 (6) | 0.0146 (7) | 0.0002 (4) | 0.0007 (5) | −0.0001 (6) |
C2 | 0.0137 (6) | 0.0192 (6) | 0.0159 (7) | −0.0022 (4) | −0.0003 (5) | 0.0005 (6) |
C3 | 0.0140 (6) | 0.0200 (7) | 0.0186 (8) | 0.0015 (4) | 0.0010 (6) | 0.0035 (7) |
C4 | 0.0221 (7) | 0.0189 (6) | 0.0207 (9) | −0.0025 (5) | 0.0026 (6) | −0.0006 (6) |
C5 | 0.0194 (6) | 0.0231 (7) | 0.0196 (8) | −0.0064 (5) | −0.0012 (7) | −0.0026 (7) |
C6 | 0.0142 (6) | 0.0261 (7) | 0.0165 (8) | −0.0005 (5) | −0.0012 (6) | 0.0000 (7) |
N1 | 0.0228 (6) | 0.0186 (6) | 0.0201 (7) | 0.0024 (4) | 0.0038 (5) | −0.0010 (5) |
N2 | 0.0188 (6) | 0.0261 (7) | 0.0233 (8) | 0.0046 (5) | 0.0015 (6) | 0.0077 (6) |
O1 | 0.0375 (7) | 0.0284 (6) | 0.0370 (9) | 0.0125 (5) | −0.0073 (7) | 0.0021 (7) |
O2 | 0.0316 (6) | 0.0216 (6) | 0.0382 (9) | −0.0039 (4) | −0.0009 (6) | −0.0069 (6) |
O3 | 0.0189 (5) | 0.0437 (8) | 0.0322 (9) | 0.0041 (5) | −0.0066 (6) | 0.0027 (7) |
O4 | 0.0348 (7) | 0.0250 (6) | 0.0524 (11) | 0.0126 (5) | 0.0022 (8) | 0.0062 (7) |
C1—C2 | 1.387 (2) | C4—C5 | 1.388 (2) |
C1—C6 | 1.387 (2) | C5—C6 | 1.389 (2) |
C1—N1 | 1.4713 (19) | N1—O2 | 1.221 (2) |
C2—C3 | 1.385 (2) | N1—O1 | 1.226 (2) |
C3—C4 | 1.389 (2) | N2—O4 | 1.221 (2) |
C3—N2 | 1.4725 (19) | N2—O3 | 1.225 (2) |
C2—C1—C6 | 123.40 (14) | C4—C5—C6 | 120.57 (14) |
C2—C1—N1 | 118.37 (14) | C1—C6—C5 | 118.46 (14) |
C6—C1—N1 | 118.22 (14) | O2—N1—O1 | 123.88 (15) |
C3—C2—C1 | 115.72 (14) | O2—N1—C1 | 118.32 (15) |
C2—C3—C4 | 123.51 (14) | O1—N1—C1 | 117.81 (15) |
C2—C3—N2 | 117.44 (13) | O4—N2—O3 | 124.28 (15) |
C4—C3—N2 | 119.05 (14) | O4—N2—C3 | 118.04 (16) |
C5—C4—C3 | 118.30 (13) | O3—N2—C3 | 117.68 (15) |
C6—C1—C2—C3 | −1.2 (3) | C4—C5—C6—C1 | 1.7 (3) |
N1—C1—C2—C3 | 178.29 (17) | C2—C1—N1—O2 | 12.6 (2) |
C1—C2—C3—C4 | 1.2 (3) | C6—C1—N1—O2 | −167.81 (17) |
C1—C2—C3—N2 | −178.81 (17) | C2—C1—N1—O1 | −167.69 (18) |
C2—C3—C4—C5 | 0.2 (3) | C6—C1—N1—O1 | 11.8 (3) |
N2—C3—C4—C5 | −179.74 (17) | C2—C3—N2—O4 | 164.3 (2) |
C3—C4—C5—C6 | −1.8 (3) | C4—C3—N2—O4 | −15.8 (3) |
C2—C1—C6—C5 | −0.2 (3) | C2—C3—N2—O3 | −15.1 (3) |
N1—C1—C6—C5 | −179.72 (16) | C4—C3—N2—O3 | 164.90 (17) |
C6H4N2O4 | Dx = 1.630 Mg m−3 |
Mr = 168.11 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 826 reflections |
a = 14.040 (4) Å | θ = 3.3–17.3° |
b = 13.208 (4) Å | µ = 0.14 mm−1 |
c = 3.694 (1) Å | T = 130 K |
V = 685.0 (3) Å3 | Prism, colourless |
Z = 4 | 0.72 × 0.33 × 0.23 mm |
F(000) = 344 |
Kuma Diffraction KM4CCD diffractometer | 1322 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.059 |
Graphite monochromator | θmax = 31.2°, θmin = 4.2° |
ω scan | h = −20→20 |
5088 measured reflections | k = −19→18 |
1422 independent reflections | l = −5→3 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.142 | Calculated w = 1/[σ2(Fo2) + (0.0504P)2 + 0.5159P] where P = (Fo2 + 2Fc2)/3 |
S = 1.18 | (Δ/σ)max < 0.001 |
1422 reflections | Δρmax = 0.32 e Å−3 |
109 parameters | Δρmin = −0.29 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 1 (2) |
C6H4N2O4 | V = 685.0 (3) Å3 |
Mr = 168.11 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 14.040 (4) Å | µ = 0.14 mm−1 |
b = 13.208 (4) Å | T = 130 K |
c = 3.694 (1) Å | 0.72 × 0.33 × 0.23 mm |
Kuma Diffraction KM4CCD diffractometer | 1322 reflections with I > 2σ(I) |
5088 measured reflections | Rint = 0.059 |
1422 independent reflections |
R[F2 > 2σ(F2)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.142 | Δρmax = 0.32 e Å−3 |
S = 1.18 | Δρmin = −0.29 e Å−3 |
1422 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
109 parameters | Absolute structure parameter: 1 (2) |
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 | ||
C1 | 0.36493 (17) | 0.63705 (17) | 0.1135 (8) | 0.0197 (5) | |
C2 | 0.44924 (16) | 0.67942 (18) | −0.0072 (8) | 0.0195 (4) | |
H2 | 0.4985 | 0.6403 | −0.1010 | 0.023* | |
C3 | 0.45566 (17) | 0.78366 (18) | 0.0203 (8) | 0.0210 (5) | |
C4 | 0.38288 (19) | 0.84386 (19) | 0.1526 (8) | 0.0249 (5) | |
H4 | 0.3900 | 0.9138 | 0.1668 | 0.030* | |
C5 | 0.29903 (18) | 0.7976 (2) | 0.2638 (9) | 0.0266 (5) | |
H5 | 0.2488 | 0.8368 | 0.3495 | 0.032* | |
C6 | 0.28984 (16) | 0.69346 (19) | 0.2476 (8) | 0.0226 (5) | |
H6 | 0.2342 | 0.6620 | 0.3254 | 0.027* | |
N1 | 0.35452 (16) | 0.52611 (16) | 0.0997 (8) | 0.0261 (5) | |
N2 | 0.54514 (16) | 0.83197 (19) | −0.0992 (8) | 0.0293 (5) | |
O1 | 0.28751 (18) | 0.48792 (17) | 0.2605 (9) | 0.0445 (6) | |
O2 | 0.41332 (16) | 0.47723 (15) | −0.0721 (8) | 0.0382 (6) | |
O3 | 0.59999 (15) | 0.7809 (2) | −0.2807 (8) | 0.0404 (6) | |
O4 | 0.56027 (18) | 0.91928 (16) | −0.0059 (10) | 0.0494 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0208 (10) | 0.0193 (10) | 0.0190 (11) | −0.0011 (7) | −0.0017 (9) | −0.0005 (9) |
C2 | 0.0165 (9) | 0.0228 (10) | 0.0192 (11) | 0.0019 (7) | 0.0004 (9) | 0.0001 (10) |
C3 | 0.0180 (10) | 0.0244 (11) | 0.0207 (12) | −0.0003 (8) | −0.0014 (9) | 0.0028 (11) |
C4 | 0.0273 (11) | 0.0220 (10) | 0.0253 (13) | 0.0039 (9) | −0.0044 (10) | −0.0012 (11) |
C5 | 0.0231 (11) | 0.0305 (13) | 0.0262 (13) | 0.0095 (9) | 0.0004 (12) | −0.0045 (12) |
C6 | 0.0145 (9) | 0.0327 (12) | 0.0205 (12) | 0.0005 (8) | 0.0013 (10) | −0.0014 (11) |
N1 | 0.0277 (10) | 0.0246 (10) | 0.0259 (11) | −0.0025 (8) | −0.0050 (10) | −0.0006 (10) |
N2 | 0.0218 (10) | 0.0359 (12) | 0.0302 (13) | −0.0059 (8) | −0.0020 (10) | 0.0091 (11) |
O1 | 0.0503 (13) | 0.0341 (11) | 0.0492 (15) | −0.0174 (9) | 0.0097 (13) | 0.0028 (12) |
O2 | 0.0399 (11) | 0.0251 (10) | 0.0495 (17) | 0.0057 (8) | 0.0008 (12) | −0.0077 (10) |
O3 | 0.0245 (9) | 0.0550 (14) | 0.0417 (15) | −0.0068 (9) | 0.0089 (11) | 0.0026 (12) |
O4 | 0.0460 (13) | 0.0297 (11) | 0.072 (2) | −0.0158 (9) | −0.0011 (15) | 0.0065 (13) |
C1—C6 | 1.383 (3) | C4—C5 | 1.389 (4) |
C1—C2 | 1.383 (3) | C5—C6 | 1.382 (4) |
C1—N1 | 1.473 (3) | N1—O1 | 1.221 (3) |
C2—C3 | 1.384 (3) | N1—O2 | 1.225 (3) |
C3—C4 | 1.384 (4) | N2—O4 | 1.222 (3) |
C3—N2 | 1.477 (3) | N2—O3 | 1.223 (4) |
C6—C1—C2 | 123.4 (2) | C6—C5—C4 | 120.3 (2) |
C6—C1—N1 | 118.2 (2) | C5—C6—C1 | 118.7 (2) |
C2—C1—N1 | 118.4 (2) | O1—N1—O2 | 123.6 (2) |
C1—C2—C3 | 115.8 (2) | O1—N1—C1 | 118.1 (2) |
C2—C3—C4 | 123.3 (2) | O2—N1—C1 | 118.4 (2) |
C2—C3—N2 | 117.6 (2) | O4—N2—O3 | 124.4 (3) |
C4—C3—N2 | 119.0 (2) | O4—N2—C3 | 118.1 (3) |
C3—C4—C5 | 118.5 (2) | O3—N2—C3 | 117.5 (2) |
C6—C1—C2—C3 | 1.3 (4) | N1—C1—C6—C5 | 179.6 (3) |
N1—C1—C2—C3 | −178.5 (3) | C6—C1—N1—O1 | −11.9 (4) |
C1—C2—C3—C4 | −1.2 (4) | C2—C1—N1—O1 | 168.0 (3) |
C1—C2—C3—N2 | 178.9 (2) | C6—C1—N1—O2 | 168.1 (3) |
C2—C3—C4—C5 | 0.0 (4) | C2—C1—N1—O2 | −12.1 (4) |
N2—C3—C4—C5 | 179.9 (3) | C2—C3—N2—O4 | −164.4 (3) |
C3—C4—C5—C6 | 1.2 (5) | C4—C3—N2—O4 | 15.7 (4) |
C4—C5—C6—C1 | −1.1 (5) | C2—C3—N2—O3 | 14.5 (4) |
C2—C1—C6—C5 | −0.2 (4) | C4—C3—N2—O3 | −165.5 (3) |
C6H4N2O4 | Dx = 1.618 Mg m−3 |
Mr = 168.11 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 958 reflections |
a = 14.052 (4) Å | θ = 3.3–16.8° |
b = 13.224 (4) Å | µ = 0.14 mm−1 |
c = 3.714 (1) Å | T = 160 K |
V = 690.1 (3) Å3 | Prism, colourless |
Z = 4 | 0.72 × 0.33 × 0.23 mm |
F(000) = 344 |
KUMA Diffraction KM4CCD diffractometer | 1077 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.100 |
Graphite monochromator | θmax = 31.2°, θmin = 4.2° |
ω scan | h = −18→20 |
3208 measured reflections | k = −18→15 |
1212 independent reflections | l = −5→2 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.155 | Calculated w = 1/[σ2(Fo2) + (0.0717P)2 + 0.2515P] where P = (Fo2 + 2Fc2)/3 |
S = 1.17 | (Δ/σ)max < 0.001 |
1212 reflections | Δρmax = 0.29 e Å−3 |
109 parameters | Δρmin = −0.32 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0 (3) |
C6H4N2O4 | V = 690.1 (3) Å3 |
Mr = 168.11 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 14.052 (4) Å | µ = 0.14 mm−1 |
b = 13.224 (4) Å | T = 160 K |
c = 3.714 (1) Å | 0.72 × 0.33 × 0.23 mm |
KUMA Diffraction KM4CCD diffractometer | 1077 reflections with I > 2σ(I) |
3208 measured reflections | Rint = 0.100 |
1212 independent reflections |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.155 | Δρmax = 0.29 e Å−3 |
S = 1.17 | Δρmin = −0.32 e Å−3 |
1212 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
109 parameters | Absolute structure parameter: 0 (3) |
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 | ||
C1 | 0.36491 (18) | 0.63742 (18) | 0.1775 (8) | 0.0248 (5) | |
C2 | 0.44928 (17) | 0.6793 (2) | 0.2991 (8) | 0.0258 (5) | |
H2 | 0.4983 | 0.6401 | 0.3927 | 0.031* | |
C3 | 0.45593 (18) | 0.7836 (2) | 0.2724 (8) | 0.0271 (5) | |
C4 | 0.3837 (2) | 0.8442 (2) | 0.1412 (9) | 0.0325 (6) | |
H4 | 0.3909 | 0.9140 | 0.1290 | 0.039* | |
C5 | 0.29996 (19) | 0.7981 (2) | 0.0279 (9) | 0.0328 (6) | |
H5 | 0.2501 | 0.8375 | −0.0587 | 0.039* | |
C6 | 0.29026 (17) | 0.6937 (2) | 0.0434 (8) | 0.0288 (5) | |
H6 | 0.2347 | 0.6625 | −0.0350 | 0.035* | |
N1 | 0.35429 (18) | 0.52676 (18) | 0.1913 (8) | 0.0334 (5) | |
N2 | 0.54545 (17) | 0.8311 (2) | 0.3934 (9) | 0.0366 (6) | |
O1 | 0.28720 (19) | 0.48880 (18) | 0.0329 (10) | 0.0555 (7) | |
O2 | 0.41256 (18) | 0.47775 (17) | 0.3635 (8) | 0.0482 (7) | |
O3 | 0.59988 (16) | 0.7797 (2) | 0.5720 (9) | 0.0507 (7) | |
O4 | 0.5604 (2) | 0.9186 (2) | 0.3036 (11) | 0.0614 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0265 (11) | 0.0251 (11) | 0.0227 (10) | 0.0007 (8) | 0.0027 (9) | 0.0007 (10) |
C2 | 0.0232 (11) | 0.0294 (12) | 0.0246 (11) | 0.0033 (8) | −0.0005 (10) | −0.0004 (10) |
C3 | 0.0236 (12) | 0.0301 (13) | 0.0275 (12) | −0.0025 (8) | 0.0022 (10) | −0.0036 (12) |
C4 | 0.0346 (13) | 0.0294 (13) | 0.0335 (14) | 0.0044 (10) | 0.0034 (12) | 0.0008 (12) |
C5 | 0.0292 (12) | 0.0373 (15) | 0.0319 (13) | 0.0086 (10) | −0.0014 (12) | 0.0055 (13) |
C6 | 0.0212 (10) | 0.0400 (14) | 0.0251 (11) | −0.0005 (9) | 0.0004 (10) | −0.0004 (12) |
N1 | 0.0368 (13) | 0.0288 (11) | 0.0346 (12) | −0.0037 (9) | 0.0042 (11) | −0.0001 (10) |
N2 | 0.0283 (12) | 0.0422 (14) | 0.0393 (13) | −0.0085 (9) | 0.0030 (11) | −0.0094 (12) |
O1 | 0.0605 (15) | 0.0437 (13) | 0.0623 (16) | −0.0211 (11) | −0.0136 (15) | −0.0017 (14) |
O2 | 0.0506 (13) | 0.0312 (11) | 0.0628 (18) | 0.0064 (9) | −0.0032 (14) | 0.0103 (12) |
O3 | 0.0282 (10) | 0.0694 (17) | 0.0546 (16) | −0.0091 (10) | −0.0103 (12) | −0.0042 (14) |
O4 | 0.0560 (15) | 0.0400 (14) | 0.088 (3) | −0.0194 (10) | 0.0015 (17) | −0.0105 (16) |
C1—C6 | 1.380 (4) | C4—C5 | 1.390 (4) |
C1—C2 | 1.385 (3) | C5—C6 | 1.388 (4) |
C1—N1 | 1.472 (3) | N1—O1 | 1.219 (4) |
C2—C3 | 1.385 (4) | N1—O2 | 1.225 (3) |
C3—C4 | 1.382 (4) | N2—O3 | 1.219 (4) |
C3—N2 | 1.476 (3) | N2—O4 | 1.222 (4) |
C6—C1—C2 | 123.6 (2) | C6—C5—C4 | 120.4 (2) |
C6—C1—N1 | 118.2 (2) | C1—C6—C5 | 118.5 (2) |
C2—C1—N1 | 118.3 (2) | O1—N1—O2 | 123.4 (3) |
C1—C2—C3 | 115.6 (2) | O1—N1—C1 | 118.1 (3) |
C4—C3—C2 | 123.6 (2) | O2—N1—C1 | 118.5 (2) |
C4—C3—N2 | 119.1 (2) | O3—N2—O4 | 124.6 (3) |
C2—C3—N2 | 117.3 (2) | O3—N2—C3 | 117.6 (3) |
C3—C4—C5 | 118.3 (2) | O4—N2—C3 | 117.8 (3) |
C6—C1—C2—C3 | −1.2 (4) | C4—C5—C6—C1 | 0.8 (5) |
N1—C1—C2—C3 | 178.7 (3) | C6—C1—N1—O1 | 11.4 (4) |
C1—C2—C3—C4 | 1.3 (4) | C2—C1—N1—O1 | −168.5 (3) |
C1—C2—C3—N2 | −179.0 (3) | C6—C1—N1—O2 | −167.9 (3) |
C2—C3—C4—C5 | −0.4 (5) | C2—C1—N1—O2 | 12.2 (4) |
N2—C3—C4—C5 | 179.9 (3) | C4—C3—N2—O3 | 165.7 (3) |
C3—C4—C5—C6 | −0.7 (5) | C2—C3—N2—O3 | −14.1 (4) |
C2—C1—C6—C5 | 0.2 (5) | C4—C3—N2—O4 | −15.3 (4) |
N1—C1—C6—C5 | −179.7 (3) | C2—C3—N2—O4 | 165.0 (3) |
C6H4N2O4 | Dx = 1.603 Mg m−3 |
Mr = 168.11 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 1607 reflections |
a = 14.069 (2) Å | θ = 3.4–24.2° |
b = 13.245 (2) Å | µ = 0.14 mm−1 |
c = 3.738 (1) Å | T = 200 K |
V = 696.6 (2) Å3 | Prism, colourless |
Z = 4 | 0.72 × 0.33 × 0.23 mm |
F(000) = 344 |
KUMA Diffraction KM4CCD diffractometer | 1330 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.068 |
Graphite monochromator | θmax = 31.2°, θmin = 4.2° |
ω scan | h = −20→20 |
5386 measured reflections | k = −19→18 |
1475 independent reflections | l = −3→5 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.146 | Calculated w = 1/[σ2(Fo2) + (0.0747P)2 + 0.2161P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
1475 reflections | Δρmax = 0.21 e Å−3 |
109 parameters | Δρmin = −0.22 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0 (2) |
C6H4N2O4 | V = 696.6 (2) Å3 |
Mr = 168.11 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 14.069 (2) Å | µ = 0.14 mm−1 |
b = 13.245 (2) Å | T = 200 K |
c = 3.738 (1) Å | 0.72 × 0.33 × 0.23 mm |
KUMA Diffraction KM4CCD diffractometer | 1330 reflections with I > 2σ(I) |
5386 measured reflections | Rint = 0.068 |
1475 independent reflections |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.146 | Δρmax = 0.21 e Å−3 |
S = 1.05 | Δρmin = −0.22 e Å−3 |
1475 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
109 parameters | Absolute structure parameter: 0 (2) |
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 | ||
C1 | 0.13479 (14) | 0.36197 (14) | 0.5644 (7) | 0.0291 (4) | |
C2 | 0.05067 (13) | 0.32061 (15) | 0.4418 (6) | 0.0294 (4) | |
H2 | 0.0020 | 0.3600 | 0.3479 | 0.035* | |
C3 | 0.04367 (14) | 0.21651 (16) | 0.4682 (7) | 0.0321 (4) | |
C4 | 0.11587 (17) | 0.15622 (16) | 0.5992 (8) | 0.0391 (5) | |
H4 | 0.1086 | 0.0865 | 0.6108 | 0.047* | |
C5 | 0.19935 (15) | 0.20174 (18) | 0.7130 (8) | 0.0402 (5) | |
H5 | 0.2490 | 0.1623 | 0.7992 | 0.048* | |
C6 | 0.20904 (14) | 0.30558 (17) | 0.6989 (7) | 0.0348 (4) | |
H6 | 0.2644 | 0.3367 | 0.7784 | 0.042* | |
N2 | −0.04551 (14) | 0.16957 (17) | 0.3447 (7) | 0.0450 (5) | |
N1 | 0.14572 (14) | 0.47250 (14) | 0.5495 (7) | 0.0401 (5) | |
O1 | 0.21314 (16) | 0.51008 (15) | 0.7081 (9) | 0.0687 (7) | |
O2 | 0.08791 (15) | 0.52161 (13) | 0.3799 (7) | 0.0585 (6) | |
O3 | −0.10015 (14) | 0.2206 (2) | 0.1703 (8) | 0.0635 (7) | |
O4 | −0.06067 (17) | 0.08222 (16) | 0.4317 (11) | 0.0768 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0295 (8) | 0.0290 (8) | 0.0289 (9) | −0.0010 (6) | 0.0013 (8) | 0.0010 (8) |
C2 | 0.0254 (8) | 0.0320 (9) | 0.0306 (9) | 0.0041 (6) | −0.0007 (8) | −0.0013 (8) |
C3 | 0.0287 (8) | 0.0347 (9) | 0.0330 (10) | −0.0005 (7) | 0.0018 (8) | −0.0045 (10) |
C4 | 0.0427 (11) | 0.0319 (9) | 0.0428 (13) | 0.0057 (8) | 0.0054 (10) | 0.0006 (10) |
C5 | 0.0340 (9) | 0.0447 (12) | 0.0418 (12) | 0.0141 (8) | −0.0018 (10) | 0.0057 (11) |
C6 | 0.0252 (8) | 0.0464 (11) | 0.0328 (10) | 0.0005 (7) | −0.0023 (8) | 0.0009 (10) |
N2 | 0.0345 (9) | 0.0514 (12) | 0.0490 (12) | −0.0103 (8) | 0.0035 (9) | −0.0129 (11) |
N1 | 0.0439 (10) | 0.0348 (8) | 0.0418 (11) | −0.0049 (7) | 0.0068 (9) | 0.0002 (9) |
O1 | 0.0746 (14) | 0.0520 (11) | 0.0795 (17) | −0.0278 (10) | −0.0154 (14) | −0.0036 (13) |
O2 | 0.0630 (12) | 0.0345 (9) | 0.0779 (18) | 0.0066 (8) | −0.0013 (12) | 0.0112 (10) |
O3 | 0.0357 (9) | 0.0848 (14) | 0.0699 (16) | −0.0090 (9) | −0.0148 (10) | −0.0041 (14) |
O4 | 0.0666 (13) | 0.0492 (11) | 0.115 (3) | −0.0255 (9) | 0.0003 (16) | −0.0139 (15) |
C1—C6 | 1.379 (3) | C4—C5 | 1.387 (3) |
C1—C2 | 1.382 (3) | C5—C6 | 1.383 (3) |
C1—N1 | 1.473 (3) | N2—O3 | 1.213 (4) |
C2—C3 | 1.386 (3) | N2—O4 | 1.221 (3) |
C3—C4 | 1.382 (3) | N1—O2 | 1.219 (3) |
C3—N2 | 1.474 (3) | N1—O1 | 1.224 (3) |
C6—C1—C2 | 123.69 (17) | C6—C5—C4 | 120.26 (19) |
C6—C1—N1 | 118.23 (18) | C1—C6—C5 | 118.55 (19) |
C2—C1—N1 | 118.08 (18) | O3—N2—O4 | 124.1 (2) |
C1—C2—C3 | 115.57 (18) | O3—N2—C3 | 118.2 (2) |
C4—C3—C2 | 123.22 (19) | O4—N2—C3 | 117.7 (2) |
C4—C3—N2 | 119.5 (2) | O2—N1—O1 | 123.5 (2) |
C2—C3—N2 | 117.24 (19) | O2—N1—C1 | 118.7 (2) |
C3—C4—C5 | 118.69 (19) | O1—N1—C1 | 117.8 (2) |
C6—C1—C2—C3 | 1.2 (4) | C4—C5—C6—C1 | −1.1 (4) |
N1—C1—C2—C3 | −178.9 (2) | C4—C3—N2—O3 | −166.3 (3) |
C1—C2—C3—C4 | −1.5 (3) | C2—C3—N2—O3 | 13.0 (4) |
C1—C2—C3—N2 | 179.2 (2) | C4—C3—N2—O4 | 15.3 (4) |
C2—C3—C4—C5 | 0.5 (4) | C2—C3—N2—O4 | −165.4 (3) |
N2—C3—C4—C5 | 179.8 (2) | C6—C1—N1—O2 | 168.3 (2) |
C3—C4—C5—C6 | 0.8 (4) | C2—C1—N1—O2 | −11.6 (3) |
C2—C1—C6—C5 | 0.0 (4) | C6—C1—N1—O1 | −11.4 (4) |
N1—C1—C6—C5 | −179.9 (2) | C2—C1—N1—O1 | 168.7 (3) |
C6H4N2O4 | Dx = 1.569 Mg m−3 |
Mr = 168.11 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 739 reflections |
a = 14.084 (4) Å | θ = 3.3–18.7° |
b = 13.292 (4) Å | µ = 0.14 mm−1 |
c = 3.802 (1) Å | T = 300 K |
V = 711.8 (3) Å3 | Prism, colourless |
Z = 4 | 0.72 × 0.33 × 0.23 mm |
F(000) = 344 |
KUMA Difffraction KM4CCD diffractometer | 1177 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.041 |
Graphite monochromator | θmax = 31.1°, θmin = 3.3° |
ω scan | h = −20→20 |
5456 measured reflections | k = −19→19 |
1486 independent reflections | l = −3→5 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.080 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.238 | Calculated w = 1/[σ2(Fo2) + (0.1144P)2 + 0.1108P] where P = (Fo2 + 2Fc2)/3 |
S = 1.20 | (Δ/σ)max < 0.001 |
1486 reflections | Δρmax = 0.25 e Å−3 |
109 parameters | Δρmin = −0.33 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 3 (4) |
C6H4N2O4 | V = 711.8 (3) Å3 |
Mr = 168.11 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 14.084 (4) Å | µ = 0.14 mm−1 |
b = 13.292 (4) Å | T = 300 K |
c = 3.802 (1) Å | 0.72 × 0.33 × 0.23 mm |
KUMA Difffraction KM4CCD diffractometer | 1177 reflections with I > 2σ(I) |
5456 measured reflections | Rint = 0.041 |
1486 independent reflections |
R[F2 > 2σ(F2)] = 0.080 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.238 | Δρmax = 0.25 e Å−3 |
S = 1.20 | Δρmin = −0.33 e Å−3 |
1486 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
109 parameters | Absolute structure parameter: 3 (4) |
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 | ||
C1 | 0.3658 (2) | 0.8609 (2) | 0.1919 (11) | 0.0454 (7) | |
C2 | 0.4494 (2) | 0.8203 (2) | 0.3163 (9) | 0.0466 (7) | |
H2 | 0.4974 | 0.8603 | 0.4095 | 0.056* | |
C3 | 0.4579 (2) | 0.7167 (3) | 0.2947 (12) | 0.0499 (8) | |
C4 | 0.3859 (3) | 0.6562 (3) | 0.1637 (14) | 0.0643 (10) | |
H4 | 0.3932 | 0.5867 | 0.1546 | 0.077* | |
C5 | 0.3029 (2) | 0.7013 (3) | 0.0464 (14) | 0.0642 (11) | |
H5 | 0.2538 | 0.6616 | −0.0405 | 0.077* | |
C6 | 0.2928 (2) | 0.8039 (3) | 0.0577 (12) | 0.0563 (9) | |
H6 | 0.2376 | 0.8343 | −0.0238 | 0.068* | |
N1 | 0.3538 (2) | 0.9703 (2) | 0.2061 (12) | 0.0660 (9) | |
N2 | 0.5462 (3) | 0.6720 (3) | 0.4234 (13) | 0.0744 (11) | |
O1 | 0.2861 (3) | 1.0070 (2) | 0.0531 (18) | 0.1129 (16) | |
O2 | 0.4113 (3) | 1.0203 (2) | 0.3696 (14) | 0.0948 (13) | |
O3 | 0.6010 (3) | 0.7246 (4) | 0.5850 (16) | 0.1042 (15) | |
O4 | 0.5618 (3) | 0.5846 (3) | 0.348 (2) | 0.133 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0466 (15) | 0.0460 (14) | 0.0435 (14) | 0.0012 (11) | 0.0053 (13) | −0.0018 (14) |
C2 | 0.0400 (14) | 0.0529 (17) | 0.0468 (16) | −0.0089 (11) | 0.0003 (14) | 0.0008 (15) |
C3 | 0.0428 (15) | 0.0542 (17) | 0.0529 (18) | 0.0017 (12) | 0.0035 (14) | 0.0062 (18) |
C4 | 0.073 (2) | 0.0472 (17) | 0.073 (3) | −0.0081 (15) | 0.013 (2) | −0.002 (2) |
C5 | 0.0539 (19) | 0.068 (2) | 0.070 (3) | −0.0192 (16) | 0.000 (2) | −0.012 (2) |
C6 | 0.0416 (15) | 0.074 (2) | 0.0529 (19) | −0.0026 (14) | −0.0026 (15) | −0.0006 (19) |
N1 | 0.071 (2) | 0.0582 (17) | 0.069 (2) | 0.0100 (15) | 0.0096 (19) | 0.0032 (18) |
N2 | 0.0566 (19) | 0.085 (3) | 0.081 (3) | 0.0206 (17) | 0.0065 (19) | 0.022 (2) |
O1 | 0.126 (3) | 0.082 (2) | 0.131 (4) | 0.046 (2) | −0.025 (3) | 0.003 (3) |
O2 | 0.107 (2) | 0.0563 (17) | 0.121 (4) | −0.0109 (16) | −0.007 (3) | −0.016 (2) |
O3 | 0.0566 (17) | 0.141 (3) | 0.115 (4) | 0.0212 (19) | −0.026 (2) | 0.009 (3) |
O4 | 0.115 (3) | 0.084 (3) | 0.199 (7) | 0.044 (2) | −0.004 (4) | 0.027 (4) |
C1—C6 | 1.375 (5) | C4—C5 | 1.387 (6) |
C1—C2 | 1.379 (5) | C5—C6 | 1.372 (6) |
C1—N1 | 1.465 (4) | N1—O2 | 1.218 (5) |
C2—C3 | 1.385 (5) | N1—O1 | 1.219 (5) |
C3—C4 | 1.386 (6) | N2—O3 | 1.208 (6) |
C3—N2 | 1.463 (5) | N2—O4 | 1.216 (6) |
C6—C1—C2 | 123.3 (3) | C6—C5—C4 | 120.4 (3) |
C6—C1—N1 | 118.3 (3) | C5—C6—C1 | 118.8 (3) |
C2—C1—N1 | 118.3 (3) | O2—N1—O1 | 123.1 (4) |
C1—C2—C3 | 116.3 (3) | O2—N1—C1 | 118.9 (3) |
C2—C3—C4 | 122.3 (3) | O1—N1—C1 | 118.0 (4) |
C2—C3—N2 | 117.2 (3) | O3—N2—O4 | 123.8 (4) |
C4—C3—N2 | 120.4 (3) | O3—N2—C3 | 118.5 (4) |
C3—C4—C5 | 118.8 (3) | O4—N2—C3 | 117.6 (5) |
C6—C1—C2—C3 | 1.1 (6) | N1—C1—C6—C5 | −179.4 (4) |
N1—C1—C2—C3 | −179.5 (3) | C6—C1—N1—O2 | 169.4 (5) |
C1—C2—C3—C4 | −1.5 (5) | C2—C1—N1—O2 | −10.1 (6) |
C1—C2—C3—N2 | 179.7 (4) | C6—C1—N1—O1 | −10.4 (6) |
C2—C3—C4—C5 | 0.8 (7) | C2—C1—N1—O1 | 170.1 (5) |
N2—C3—C4—C5 | 179.5 (4) | C2—C3—N2—O3 | 10.2 (7) |
C3—C4—C5—C6 | 0.5 (7) | C4—C3—N2—O3 | −168.6 (5) |
C4—C5—C6—C1 | −0.9 (7) | C2—C3—N2—O4 | −166.8 (5) |
C2—C1—C6—C5 | 0.1 (6) | C4—C3—N2—O4 | 14.3 (7) |
Experimental details
(100) | (130) | (160) | (200) | |
Crystal data | ||||
Chemical formula | C6H4N2O4 | C6H4N2O4 | C6H4N2O4 | C6H4N2O4 |
Mr | 168.11 | 168.11 | 168.11 | 168.11 |
Crystal system, space group | Orthorhombic, Pna21 | Orthorhombic, Pna21 | Orthorhombic, Pna21 | Orthorhombic, Pna21 |
Temperature (K) | 100 | 130 | 160 | 200 |
a, b, c (Å) | 14.024 (2), 13.182 (2), 3.677 (1) | 14.040 (4), 13.208 (4), 3.694 (1) | 14.052 (4), 13.224 (4), 3.714 (1) | 14.069 (2), 13.245 (2), 3.738 (1) |
V (Å3) | 679.7 (2) | 685.0 (3) | 690.1 (3) | 696.6 (2) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.14 | 0.14 | 0.14 | 0.14 |
Crystal size (mm) | 0.72 × 0.33 × 0.23 | 0.72 × 0.33 × 0.23 | 0.72 × 0.33 × 0.23 | 0.72 × 0.33 × 0.23 |
Data collection | ||||
Diffractometer | KUMA Diffraction KM4CCD diffractometer | Kuma Diffraction KM4CCD diffractometer | KUMA Diffraction KM4CCD diffractometer | KUMA Diffraction KM4CCD diffractometer |
Absorption correction | – | – | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5634, 1448, 1388 | 5088, 1422, 1322 | 3208, 1212, 1077 | 5386, 1475, 1330 |
Rint | 0.069 | 0.059 | 0.100 | 0.068 |
(sin θ/λ)max (Å−1) | 0.729 | 0.728 | 0.729 | 0.729 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.123, 1.16 | 0.056, 0.142, 1.18 | 0.054, 0.155, 1.17 | 0.054, 0.146, 1.05 |
No. of reflections | 1448 | 1422 | 1212 | 1475 |
No. of parameters | 109 | 109 | 109 | 109 |
No. of restraints | 1 | 1 | 1 | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.28, −0.32 | 0.32, −0.29 | 0.29, −0.32 | 0.21, −0.22 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | −0.7 (14) | 1 (2) | 0 (3) | 0 (2) |
(300) | |
Crystal data | |
Chemical formula | C6H4N2O4 |
Mr | 168.11 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 300 |
a, b, c (Å) | 14.084 (4), 13.292 (4), 3.802 (1) |
V (Å3) | 711.8 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.14 |
Crystal size (mm) | 0.72 × 0.33 × 0.23 |
Data collection | |
Diffractometer | KUMA Difffraction KM4CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5456, 1486, 1177 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.727 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.080, 0.238, 1.20 |
No. of reflections | 1486 |
No. of parameters | 109 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.25, −0.33 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | 3 (4) |
Computer programs: KUMA KM4CCD software, 1999, KUMA Diffraction Km4CCD software, 1999, KUMA Diffraction KM4CCD software, 1999, SHELXS97 (Sheldrick, 1997), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), ORTEP-3 (Farrugia,1997), SHELXL97 (SHeldrick, 1997).