The structure of the title compound, C
7H
4N
2O
5, was determined from low-temperature data (at about 110 K). It reveals a stacked-layered organization of the molecules with C—H
O interactions within the layers.
Supporting information
CCDC reference: 630046
Key indicators
- Single-crystal X-ray study
- T = 110 K
- Mean (C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.127
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7 .. O14 .. 2.62 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al.,
2006); software used to prepare material for publication: SHELXL97.
3,5-dinitrobenzaldehyde
top
Crystal data top
C7H4N2O5 | F(000) = 400 |
Mr = 196.12 | Dx = 1.694 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1944 reflections |
a = 8.2791 (2) Å | θ = 2.7–30.5° |
b = 6.2091 (1) Å | µ = 0.15 mm−1 |
c = 14.9903 (4) Å | T = 110 K |
β = 93.5895 (11)° | Prism, colourless |
V = 769.08 (3) Å3 | 0.35 × 0.30 × 0.20 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD diffractometer | 1793 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 30.5°, θmin = 2.7° |
Detector resolution: 12.8 pixels mm-1 | h = −11→11 |
0.9° φ and ω scans | k = −8→8 |
6627 measured reflections | l = −21→21 |
2321 independent reflections | |
Refinement top
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | All H-atom parameters refined |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0766P)2 + 0.0648P] where P = (Fo2 + 2Fc2)/3 |
2321 reflections | (Δ/σ)max = 0.028 |
143 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
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 | −0.11462 (14) | 0.25315 (18) | 0.06623 (8) | 0.0219 (2) | |
C2 | −0.17585 (14) | 0.27053 (18) | 0.15027 (8) | 0.0223 (2) | |
H2 | −0.290 (2) | 0.265 (3) | 0.1556 (13) | 0.043 (5)* | |
C3 | −0.06840 (13) | 0.30341 (18) | 0.22377 (8) | 0.0209 (2) | |
C4 | 0.09769 (13) | 0.32345 (18) | 0.21749 (7) | 0.0210 (2) | |
H4 | 0.1744 (16) | 0.341 (2) | 0.2700 (10) | 0.026 (4)* | |
C5 | 0.15301 (13) | 0.30645 (18) | 0.13217 (8) | 0.0212 (2) | |
C6 | 0.05220 (14) | 0.27122 (18) | 0.05634 (8) | 0.0219 (2) | |
H6 | 0.095 (2) | 0.258 (2) | −0.0008 (13) | 0.038 (4)* | |
C7 | −0.22741 (14) | 0.2165 (2) | −0.01344 (8) | 0.0248 (3) | |
H7 | −0.341 (2) | 0.205 (2) | −0.0032 (11) | 0.033 (4)* | |
O8 | −0.18243 (11) | 0.20481 (15) | −0.08846 (6) | 0.0290 (2) | |
N9 | −0.13267 (11) | 0.32251 (16) | 0.31259 (6) | 0.0239 (2) | |
O10 | −0.04542 (10) | 0.40232 (16) | 0.37283 (5) | 0.0303 (2) | |
O11 | −0.27224 (11) | 0.26105 (16) | 0.32081 (6) | 0.0325 (2) | |
N12 | 0.32780 (11) | 0.33081 (17) | 0.12229 (7) | 0.0244 (2) | |
O13 | 0.41672 (10) | 0.35595 (18) | 0.19013 (6) | 0.0332 (2) | |
O14 | 0.37481 (11) | 0.32715 (18) | 0.04632 (6) | 0.0345 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0216 (5) | 0.0215 (5) | 0.0218 (5) | 0.0013 (4) | −0.0042 (4) | 0.0012 (4) |
C2 | 0.0195 (5) | 0.0227 (5) | 0.0241 (6) | 0.0004 (4) | −0.0026 (4) | 0.0028 (4) |
C3 | 0.0211 (5) | 0.0215 (5) | 0.0200 (5) | 0.0006 (4) | 0.0000 (4) | 0.0017 (4) |
C4 | 0.0207 (5) | 0.0209 (5) | 0.0208 (5) | 0.0014 (4) | −0.0033 (4) | 0.0001 (4) |
C5 | 0.0185 (5) | 0.0222 (5) | 0.0227 (5) | 0.0015 (4) | −0.0003 (4) | 0.0006 (4) |
C6 | 0.0236 (5) | 0.0218 (5) | 0.0199 (5) | 0.0018 (4) | −0.0013 (4) | 0.0003 (4) |
C7 | 0.0233 (5) | 0.0267 (6) | 0.0235 (5) | 0.0004 (4) | −0.0051 (4) | 0.0007 (4) |
O8 | 0.0285 (4) | 0.0353 (5) | 0.0225 (4) | 0.0009 (3) | −0.0047 (3) | −0.0016 (3) |
N9 | 0.0225 (5) | 0.0270 (5) | 0.0219 (5) | 0.0023 (4) | −0.0006 (4) | 0.0017 (4) |
O10 | 0.0269 (4) | 0.0423 (5) | 0.0212 (4) | 0.0025 (4) | −0.0034 (3) | −0.0024 (4) |
O11 | 0.0244 (4) | 0.0423 (5) | 0.0310 (5) | −0.0049 (4) | 0.0046 (4) | 0.0011 (4) |
N12 | 0.0195 (4) | 0.0287 (5) | 0.0248 (5) | 0.0023 (4) | −0.0004 (4) | −0.0015 (4) |
O13 | 0.0201 (4) | 0.0498 (6) | 0.0291 (5) | 0.0009 (4) | −0.0046 (3) | −0.0065 (4) |
O14 | 0.0245 (4) | 0.0532 (6) | 0.0262 (4) | 0.0029 (4) | 0.0033 (4) | −0.0009 (4) |
Geometric parameters (Å, º) top
C1—C2 | 1.3913 (16) | C5—C6 | 1.3848 (16) |
C1—C6 | 1.4028 (16) | C5—N12 | 1.4716 (14) |
C1—C7 | 1.4867 (16) | C6—H6 | 0.952 (18) |
C2—C3 | 1.3872 (16) | C7—O8 | 1.2087 (15) |
C2—H2 | 0.958 (19) | C7—H7 | 0.967 (17) |
C3—C4 | 1.3898 (15) | N9—O10 | 1.2251 (13) |
C3—N9 | 1.4693 (14) | N9—O11 | 1.2304 (13) |
C4—C5 | 1.3892 (15) | N12—O14 | 1.2266 (13) |
C4—H4 | 0.987 (15) | N12—O13 | 1.2275 (13) |
| | | |
C2—C1—C6 | 120.43 (10) | C4—C5—N12 | 117.89 (10) |
C2—C1—C7 | 119.55 (10) | C5—C6—C1 | 118.21 (11) |
C6—C1—C7 | 120.03 (10) | C5—C6—H6 | 120.8 (10) |
C3—C2—C1 | 118.60 (10) | C1—C6—H6 | 121.0 (10) |
C3—C2—H2 | 121.9 (12) | O8—C7—C1 | 122.82 (11) |
C1—C2—H2 | 119.4 (12) | O8—C7—H7 | 120.3 (10) |
C2—C3—C4 | 123.19 (11) | C1—C7—H7 | 116.9 (10) |
C2—C3—N9 | 118.75 (10) | O10—N9—O11 | 124.46 (10) |
C4—C3—N9 | 118.04 (10) | O10—N9—C3 | 118.05 (9) |
C5—C4—C3 | 116.12 (10) | O11—N9—C3 | 117.47 (9) |
C5—C4—H4 | 120.7 (8) | O14—N12—O13 | 124.26 (10) |
C3—C4—H4 | 123.1 (8) | O14—N12—C5 | 117.56 (9) |
C6—C5—C4 | 123.45 (10) | O13—N12—C5 | 118.18 (9) |
C6—C5—N12 | 118.66 (10) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O13i | 0.958 (19) | 2.573 (19) | 3.5027 (14) | 163.7 (15) |
C4—H4···O8ii | 0.987 (15) | 2.381 (15) | 3.3382 (14) | 163.1 (12) |
C7—H7···O10iii | 0.967 (17) | 2.523 (17) | 3.1338 (14) | 121.1 (12) |
C7—H7···O14i | 0.967 (17) | 2.621 (17) | 3.5340 (15) | 157.7 (12) |
Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1/2, z+1/2; (iii) x−1/2, −y+1/2, z−1/2. |