Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801013022/cv6049sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801013022/cv6049Isup2.hkl |
CCDC reference: 172202
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.046
- wR factor = 0.133
- Data-to-parameter ratio = 8.9
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLG_01 _reflns_number_observed is an old dataname which has been superseded by _reflns_number_gt REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 1061 Count of symmetry unique reflns 1060 Completeness (_total/calc) 100.09% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1 Fraction of Friedel pairs measured 0.001 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
Single crystals of the title chiral compound were obtained from a methanol solution containing 2,6- and 2,4-dinitrotoluene when we tried to separate the isomers.
H atoms were located in calculated positions and ridden on parent C atoms during refinements. The absolute configuration could not be reliably determined.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1985a, 1992a); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1985b, 1992b); program(s) used to solve structure: SHELXS93 (Sheldrick, 1993); program(s) used to refine structure: SHELXL93; molecular graphics: XP (Siemens, 1994).
Fig. 1. View of the crystal packing of the title compound with 30% probability displacement ellipsoids, showing the overlap of adjacent benzene rings. H atoms have been omitted for clarity. |
C7H6N2O4 | Dx = 1.548 Mg m−3 |
Mr = 182.14 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 20 reflections |
a = 7.830 (2) Å | θ = 11.7–21.5° |
b = 13.683 (3) Å | µ = 0.13 mm−1 |
c = 7.296 (2) Å | T = 293 K |
V = 781.7 (3) Å3 | Prismatic, yellow |
Z = 4 | 0.30 × 0.24 × 0.20 mm |
F(000) = 376 |
Rigaku AFC-7R diffractometer | 906 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 27.5°, θmin = 3.0° |
ω/2θ scans | h = 0→10 |
Absorption correction: psi scan (North et al., 1968) | k = 0→17 |
Tmin = 0.963, Tmax = 0.974 | l = 0→9 |
1061 measured reflections | 3 standard reflections every 100 reflections |
1061 independent reflections | intensity decay: 0.3% |
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)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0748P)2 + 0.2426P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
1061 reflections | Δρmax = 0.27 e Å−3 |
119 parameters | Δρmin = −0.23 e Å−3 |
0 restraints | Extinction correction: SHELXL93, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0719 (109) |
C7H6N2O4 | V = 781.7 (3) Å3 |
Mr = 182.14 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.830 (2) Å | µ = 0.13 mm−1 |
b = 13.683 (3) Å | T = 293 K |
c = 7.296 (2) Å | 0.30 × 0.24 × 0.20 mm |
Rigaku AFC-7R diffractometer | 906 reflections with I > 2σ(I) |
Absorption correction: psi scan (North et al., 1968) | Rint = 0.000 |
Tmin = 0.963, Tmax = 0.974 | 3 standard reflections every 100 reflections |
1061 measured reflections | intensity decay: 0.3% |
1061 independent reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.27 e Å−3 |
1061 reflections | Δρmin = −0.23 e Å−3 |
119 parameters |
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. 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 | ||
O1 | 0.8388 (3) | 0.23852 (14) | 0.7794 (4) | 0.0640 (7) | |
O2 | 0.6725 (4) | 0.2359 (2) | 1.0143 (5) | 0.0709 (8) | |
O3 | 0.3958 (3) | −0.1192 (2) | 1.0183 (4) | 0.0665 (7) | |
O4 | 0.5395 (4) | −0.2154 (2) | 0.8452 (5) | 0.0846 (10) | |
N1 | 0.7602 (3) | 0.1962 (2) | 0.8992 (4) | 0.0486 (6) | |
N2 | 0.5215 (3) | −0.1393 (2) | 0.9266 (4) | 0.0503 (6) | |
C1 | 0.6289 (3) | 0.0320 (2) | 0.9135 (4) | 0.0395 (6) | |
C2 | 0.7764 (3) | 0.0884 (2) | 0.9082 (5) | 0.0413 (6) | |
C3 | 0.9412 (4) | 0.0525 (2) | 0.9081 (5) | 0.0475 (7) | |
H3 | 1.0342 (4) | 0.0947 (2) | 0.9025 (5) | 0.057* | |
C4 | 0.9651 (4) | −0.0477 (2) | 0.9165 (5) | 0.0489 (7) | |
H4 | 1.0748 (4) | −0.0737 (2) | 0.9209 (5) | 0.059* | |
C5 | 0.8256 (4) | −0.1084 (2) | 0.9182 (5) | 0.0471 (7) | |
H5 | 0.8401 (4) | −0.1759 (2) | 0.9188 (5) | 0.057* | |
C6 | 0.6635 (3) | −0.0686 (2) | 0.9191 (4) | 0.0400 (6) | |
C7 | 0.4516 (4) | 0.0738 (2) | 0.8999 (6) | 0.0528 (8) | |
H7A | 0.3695 (4) | 0.0218 (2) | 0.9067 (6) | 0.079* | |
H7B | 0.4392 (4) | 0.1075 (2) | 0.7853 (6) | 0.079* | |
H7C | 0.4330 (4) | 0.1187 (2) | 0.9990 (6) | 0.079* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0618 (13) | 0.0413 (10) | 0.089 (2) | −0.0103 (11) | −0.0006 (14) | 0.0130 (12) |
O2 | 0.078 (2) | 0.0411 (12) | 0.094 (2) | 0.0051 (12) | 0.013 (2) | −0.0150 (12) |
O3 | 0.0462 (12) | 0.0585 (13) | 0.095 (2) | −0.0100 (10) | 0.0075 (13) | 0.0034 (14) |
O4 | 0.078 (2) | 0.0458 (12) | 0.130 (3) | −0.0177 (13) | 0.001 (2) | −0.027 (2) |
N1 | 0.0455 (12) | 0.0305 (10) | 0.070 (2) | −0.0027 (9) | −0.0062 (14) | 0.0001 (12) |
N2 | 0.0430 (12) | 0.0389 (11) | 0.069 (2) | −0.0069 (10) | −0.0044 (13) | 0.0003 (13) |
C1 | 0.0363 (12) | 0.0333 (12) | 0.0489 (13) | 0.0032 (10) | 0.0002 (13) | 0.0006 (12) |
C2 | 0.0407 (13) | 0.0298 (11) | 0.053 (2) | −0.0001 (10) | 0.0006 (15) | −0.0022 (12) |
C3 | 0.0378 (13) | 0.0425 (14) | 0.062 (2) | −0.0053 (11) | −0.004 (2) | 0.0046 (15) |
C4 | 0.0345 (12) | 0.0471 (14) | 0.065 (2) | 0.0072 (11) | 0.000 (2) | 0.0036 (15) |
C5 | 0.0461 (14) | 0.0340 (12) | 0.061 (2) | 0.0068 (11) | −0.001 (2) | −0.0013 (13) |
C6 | 0.0379 (12) | 0.0299 (11) | 0.0523 (15) | −0.0041 (10) | −0.0014 (14) | −0.0009 (12) |
C7 | 0.0397 (13) | 0.0395 (13) | 0.079 (2) | 0.0081 (12) | 0.002 (2) | 0.005 (2) |
O1—N1 | 1.216 (3) | C3—C4 | 1.386 (4) |
O2—N1 | 1.213 (4) | C3—H3 | 0.93 |
O3—N2 | 1.221 (3) | C4—C5 | 1.372 (4) |
O4—N2 | 1.206 (4) | C4—H4 | 0.93 |
N1—C2 | 1.482 (3) | C5—C6 | 1.382 (4) |
N2—C6 | 1.476 (3) | C5—H5 | 0.93 |
C1—C2 | 1.389 (4) | C7—H7A | 0.96 |
C1—C6 | 1.404 (3) | C7—H7B | 0.96 |
C1—C7 | 1.505 (4) | C7—H7C | 0.96 |
C2—C3 | 1.380 (4) | ||
O1—N1—O2 | 124.8 (2) | C5—C4—C3 | 119.5 (3) |
O1—N1—C2 | 117.5 (3) | C5—C4—H4 | 120.3 |
O2—N1—C2 | 117.6 (3) | C3—C4—H4 | 120.3 |
O4—N2—O3 | 124.0 (3) | C4—C5—C6 | 119.5 (2) |
O4—N2—C6 | 117.4 (3) | C4—C5—H5 | 120.2 |
O3—N2—C6 | 118.7 (2) | C6—C5—H5 | 120.24 |
C2—C1—C6 | 112.6 (2) | C5—C6—C1 | 124.3 (2) |
C2—C1—C7 | 123.7 (2) | C5—C6—N2 | 115.7 (2) |
C6—C1—C7 | 123.5 (2) | C1—C6—N2 | 120.0 (2) |
C3—C2—C1 | 125.4 (2) | C1—C7—H7A | 109.47 |
C3—C2—N1 | 115.7 (2) | C1—C7—H7B | 109.5 |
C1—C2—N1 | 118.8 (2) | H7A—C7—H7B | 109.5 |
C2—C3—C4 | 118.6 (3) | C1—C7—H7C | 109.5 |
C2—C3—H3 | 120.7 | H7A—C7—H7C | 109.5 |
C4—C3—H3 | 120.7 | H7B—C7—H7C | 109.5 |
Experimental details
Crystal data | |
Chemical formula | C7H6N2O4 |
Mr | 182.14 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 7.830 (2), 13.683 (3), 7.296 (2) |
V (Å3) | 781.7 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.30 × 0.24 × 0.20 |
Data collection | |
Diffractometer | Rigaku AFC-7R diffractometer |
Absorption correction | Psi scan (North et al., 1968) |
Tmin, Tmax | 0.963, 0.974 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1061, 1061, 906 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.133, 1.05 |
No. of reflections | 1061 |
No. of parameters | 119 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.23 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1985a, 1992a), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1985b, 1992b), SHELXS93 (Sheldrick, 1993), SHELXL93, XP (Siemens, 1994).
O1—N1 | 1.216 (3) | O4—N2 | 1.206 (4) |
O2—N1 | 1.213 (4) | N1—C2 | 1.482 (3) |
O3—N2 | 1.221 (3) | N2—C6 | 1.476 (3) |
O1—N1—O2 | 124.8 (2) | O4—N2—C6 | 117.4 (3) |
O1—N1—C2 | 117.5 (3) | O3—N2—C6 | 118.7 (2) |
O2—N1—C2 | 117.6 (3) | C2—C1—C6 | 112.6 (2) |
O4—N2—O3 | 124.0 (3) |
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