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The meta-dinitrobenzene crystal structure has been determined at five temperatures in the 100-300 K temperature range. The thermal expansion coefficients have been calculated from the temperature variation of the lattice parameters. Rigid-body motion analysis with allowance for large-amplitude internal motions provided the T, L and S tensors' values at the temperatures studied and was used to characterize the torsional motion of two nitro groups in the molecule. Frequencies of the translational and librational modes and of the torsional modes of the nitro groups have been compared with the wave numbers at the maximum of bands in the low-frequency Raman and IR spectra. Ab initio calculations were performed in order to assess the contribution from large-amplitude internal motions to the static first-order hyperpolarizability of the m-dinitrobenzene molecule.
Supporting information
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.
(100) 1,3-dinitrobenzene
top
Crystal data top
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 | |
Data collection top
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 top
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) |
Crystal data top
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 |
Data collection top
KUMA Diffraction KM4CCD diffractometer | 1388 reflections with I > 2σ(I) |
5634 measured reflections | Rint = 0.069 |
1448 independent reflections | |
Refinement top
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 | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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) | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
(130) 1,3-dinitrobenzene
top
Crystal data top
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 | |
Data collection top
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 top
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) |
Crystal data top
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 |
Data collection top
Kuma Diffraction KM4CCD diffractometer | 1322 reflections with I > 2σ(I) |
5088 measured reflections | Rint = 0.059 |
1422 independent reflections | |
Refinement top
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 | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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) | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
(160) 1,3-dinitrobenzene
top
Crystal data top
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 | |
Data collection top
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 top
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) |
Crystal data top
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 |
Data collection top
KUMA Diffraction KM4CCD diffractometer | 1077 reflections with I > 2σ(I) |
3208 measured reflections | Rint = 0.100 |
1212 independent reflections | |
Refinement top
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 | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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) | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
(200) 1,3-dinitrobenzene
top
Crystal data top
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 | |
Data collection top
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 top
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) |
Crystal data top
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 |
Data collection top
KUMA Diffraction KM4CCD diffractometer | 1330 reflections with I > 2σ(I) |
5386 measured reflections | Rint = 0.068 |
1475 independent reflections | |
Refinement top
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 | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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) | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
(300) 1,3-dinitrobenzene
top
Crystal data top
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 | |
Data collection top
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 top
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) |
Crystal data top
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 |
Data collection top
KUMA Difffraction KM4CCD diffractometer | 1177 reflections with I > 2σ(I) |
5456 measured reflections | Rint = 0.041 |
1486 independent reflections | |
Refinement top
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 | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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) | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
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