Buy article online - an online subscription or single-article purchase is required to access this article.
The title compound, C
8H
5NO
5, consists of a cyclic diether (1,3-dioxalene) fused to 3-nitrobenzaldehyde. In the crystal structure, symmetry-related molecules are linked by C—H
O hydrogen bonds, forming a sheet-like structure parallel to the
ab plane. These sheets are further linked by C—H
O hydrogen bonds, forming a three-dimensional network.
Supporting information
CCDC reference: 628046
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.118
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.110
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT432_ALERT_2_C Short Inter X...Y Contact O5 .. C7 .. 2.99 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2006); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
6-Nitro-1,3-benzodioxole-4-carbaldehyde
top
Crystal data top
C8H5NO5 | F(000) = 400 |
Mr = 195.13 | Dx = 1.696 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5272 reflections |
a = 7.462 (1) Å | θ = 2.6–29.6° |
b = 14.166 (2) Å | µ = 0.15 mm−1 |
c = 7.3202 (10) Å | T = 173 K |
β = 98.975 (11)° | Plate, yellow |
V = 764.3 (2) Å3 | 0.40 × 0.40 × 0.15 mm |
Z = 4 | |
Data collection top
Stoe IPDS-2 diffractometer | 1502 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.110 |
Graphite monochromator | θmax = 29.3°, θmin = 2.8° |
Detector resolution: 6.67 pixels mm-1 | h = −10→9 |
φ and ω scans | k = −19→19 |
7266 measured reflections | l = −10→9 |
2013 independent reflections | |
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 | All H-atom parameters refined |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0518P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
2013 reflections | Δρmax = 0.38 e Å−3 |
148 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.034 (5) |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
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 | |
O1 | 0.74307 (17) | 1.05449 (8) | 0.12610 (18) | 0.0408 (4) | |
O2 | 0.70215 (14) | 0.65053 (7) | 0.27721 (14) | 0.0269 (3) | |
O3 | 0.87287 (14) | 0.76767 (7) | 0.16668 (14) | 0.0264 (3) | |
O4 | 0.1829 (2) | 0.95479 (9) | 0.3843 (2) | 0.0484 (4) | |
O5 | 0.16909 (16) | 0.81293 (9) | 0.48801 (17) | 0.0404 (4) | |
N1 | 0.24299 (18) | 0.87460 (9) | 0.40923 (18) | 0.0307 (4) | |
C1 | 0.67432 (19) | 0.90000 (9) | 0.21585 (18) | 0.0231 (4) | |
C2 | 0.5105 (2) | 0.92180 (9) | 0.27806 (19) | 0.0247 (4) | |
C3 | 0.41175 (19) | 0.85088 (9) | 0.34309 (18) | 0.0238 (4) | |
C4 | 0.4629 (2) | 0.75554 (9) | 0.35097 (18) | 0.0231 (4) | |
C5 | 0.62143 (19) | 0.73630 (9) | 0.29023 (18) | 0.0216 (4) | |
C6 | 0.72612 (18) | 0.80620 (9) | 0.22424 (17) | 0.0212 (3) | |
C7 | 0.8735 (2) | 0.66945 (10) | 0.2188 (2) | 0.0283 (4) | |
C8 | 0.7846 (2) | 0.97229 (10) | 0.1421 (2) | 0.0284 (4) | |
H2 | 0.466 (3) | 0.9874 (14) | 0.276 (3) | 0.036 (5)* | |
H4 | 0.387 (3) | 0.7099 (13) | 0.396 (3) | 0.034 (5)* | |
H7A | 0.976 (3) | 0.6597 (13) | 0.325 (3) | 0.035 (5)* | |
H7B | 0.883 (3) | 0.6311 (14) | 0.106 (3) | 0.040 (5)* | |
H8 | 0.892 (3) | 0.9531 (15) | 0.092 (3) | 0.042 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0411 (7) | 0.0197 (5) | 0.0607 (8) | −0.0024 (4) | 0.0048 (6) | 0.0064 (5) |
O2 | 0.0266 (6) | 0.0173 (4) | 0.0390 (5) | 0.0031 (4) | 0.0122 (4) | 0.0013 (4) |
O3 | 0.0245 (6) | 0.0199 (5) | 0.0368 (5) | 0.0024 (4) | 0.0114 (4) | 0.0030 (4) |
O4 | 0.0396 (7) | 0.0339 (6) | 0.0753 (9) | 0.0142 (5) | 0.0207 (7) | 0.0026 (6) |
O5 | 0.0324 (7) | 0.0393 (6) | 0.0538 (7) | −0.0015 (5) | 0.0205 (6) | −0.0010 (5) |
N1 | 0.0252 (7) | 0.0287 (6) | 0.0390 (7) | 0.0029 (5) | 0.0080 (6) | −0.0050 (5) |
C1 | 0.0227 (7) | 0.0184 (6) | 0.0274 (6) | −0.0007 (5) | 0.0019 (5) | −0.0002 (4) |
C2 | 0.0261 (7) | 0.0190 (6) | 0.0281 (6) | 0.0025 (5) | 0.0011 (5) | −0.0028 (5) |
C3 | 0.0200 (7) | 0.0244 (6) | 0.0272 (6) | 0.0018 (5) | 0.0047 (5) | −0.0021 (5) |
C4 | 0.0234 (7) | 0.0212 (6) | 0.0249 (6) | −0.0019 (5) | 0.0049 (5) | −0.0003 (5) |
C5 | 0.0236 (7) | 0.0159 (6) | 0.0254 (6) | 0.0007 (5) | 0.0039 (5) | −0.0003 (4) |
C6 | 0.0189 (6) | 0.0217 (6) | 0.0230 (6) | 0.0004 (4) | 0.0034 (5) | −0.0014 (4) |
C7 | 0.0276 (8) | 0.0203 (6) | 0.0394 (8) | 0.0038 (5) | 0.0125 (6) | 0.0044 (5) |
C8 | 0.0293 (8) | 0.0215 (6) | 0.0335 (7) | −0.0048 (5) | 0.0023 (6) | 0.0009 (5) |
Geometric parameters (Å, º) top
O1—C8 | 1.2060 (18) | C1—C8 | 1.468 (2) |
O2—C5 | 1.3660 (17) | C2—C3 | 1.3742 (19) |
O2—C7 | 1.4353 (18) | C3—C4 | 1.4022 (18) |
O3—C6 | 1.3485 (17) | C4—C5 | 1.355 (2) |
O3—C7 | 1.4426 (17) | C5—C6 | 1.3935 (19) |
O4—N1 | 1.2244 (18) | C2—H2 | 0.99 (2) |
O5—N1 | 1.2244 (18) | C4—H4 | 0.95 (2) |
N1—C3 | 1.457 (2) | C7—H7A | 1.01 (2) |
C1—C2 | 1.404 (2) | C7—H7B | 1.00 (2) |
C1—C6 | 1.3825 (18) | C8—H8 | 0.97 (2) |
| | | |
O1···C4i | 3.2531 (18) | C1···O2vii | 3.3277 (17) |
O1···C7ii | 3.334 (2) | C2···O1iii | 3.271 (2) |
O1···C2iii | 3.271 (2) | C4···O5vii | 3.3150 (19) |
O2···O4iv | 3.1841 (17) | C4···O1iv | 3.2531 (18) |
O2···C1v | 3.3277 (17) | C4···C5v | 3.2504 (19) |
O2···C6v | 3.3066 (17) | C4···C6v | 3.2271 (19) |
O2···O3 | 2.3136 (15) | C5···C4vii | 3.2504 (19) |
O2···O3v | 3.1561 (15) | C5···O3v | 3.0829 (17) |
O2···C8v | 3.1666 (18) | C5···C6v | 3.2081 (18) |
O3···O5vi | 3.0344 (17) | C6···O3v | 3.4172 (17) |
O3···C5vii | 3.0829 (17) | C6···O2vii | 3.3066 (17) |
O3···O5viii | 2.9668 (17) | C6···C4vii | 3.2271 (19) |
O3···O2 | 2.3136 (15) | C6···C5vii | 3.2081 (18) |
O3···C6vii | 3.4172 (17) | C7···O1xi | 3.334 (2) |
O3···O2vii | 3.1561 (15) | C7···O4iv | 3.146 (2) |
O3···C7vii | 3.3981 (18) | C7···O5vi | 3.395 (2) |
O4···O2i | 3.1841 (17) | C7···O5viii | 2.991 (2) |
O4···C8ix | 3.224 (2) | C7···O3v | 3.3981 (18) |
O4···C7i | 3.146 (2) | C8···O2vii | 3.1666 (18) |
O5···C7ix | 3.395 (2) | C8···O4vi | 3.224 (2) |
O5···O3ix | 3.0344 (17) | C1···H7Bv | 3.06 (2) |
O5···C4v | 3.3150 (19) | C6···H7Bv | 2.99 (2) |
O5···C7x | 2.991 (2) | H2···O1 | 2.66 (2) |
O5···O3x | 2.9668 (17) | H2···O4 | 2.41 (2) |
O1···H2 | 2.66 (2) | H2···O2i | 2.63 (2) |
O1···H7Aii | 2.55 (2) | H4···O5 | 2.36 (2) |
O1···H4i | 2.401 (19) | H4···O1iv | 2.401 (19) |
O2···H2iv | 2.63 (2) | H7A···O5vi | 2.77 (2) |
O2···H8v | 2.91 (2) | H7A···O1xi | 2.55 (2) |
O3···H7Avii | 2.92 (2) | H7A···O3v | 2.92 (2) |
O3···H8 | 2.69 (2) | H7B···O4iv | 2.55 (2) |
O4···H8ix | 2.80 (2) | H7B···O5viii | 2.55 (2) |
O4···H7Bi | 2.55 (2) | H7B···C1vii | 3.06 (2) |
O4···H2 | 2.41 (2) | H7B···C6vii | 2.99 (2) |
O5···H4 | 2.36 (2) | H8···O3 | 2.69 (2) |
O5···H7Aix | 2.77 (2) | H8···O4vi | 2.80 (2) |
O5···H7Bx | 2.55 (2) | H8···O2vii | 2.91 (2) |
| | | |
C5—O2—C7 | 106.12 (11) | O3—C6—C1 | 127.60 (12) |
C6—O3—C7 | 106.08 (11) | O3—C6—C5 | 110.31 (11) |
O4—N1—O5 | 123.42 (14) | C1—C6—C5 | 122.03 (13) |
O4—N1—C3 | 118.67 (13) | O2—C7—O3 | 107.01 (11) |
O5—N1—C3 | 117.91 (12) | O1—C8—C1 | 123.98 (14) |
C2—C1—C6 | 116.65 (12) | C1—C2—H2 | 120.7 (13) |
C2—C1—C8 | 122.15 (12) | C3—C2—H2 | 119.8 (13) |
C6—C1—C8 | 121.19 (13) | C3—C4—H4 | 119.7 (13) |
C1—C2—C3 | 119.52 (12) | C5—C4—H4 | 125.1 (13) |
N1—C3—C2 | 118.97 (12) | O2—C7—H7A | 110.3 (12) |
N1—C3—C4 | 116.89 (12) | O2—C7—H7B | 109.0 (13) |
C2—C3—C4 | 124.14 (13) | O3—C7—H7A | 107.8 (11) |
C3—C4—C5 | 115.23 (12) | O3—C7—H7B | 107.7 (12) |
O2—C5—C4 | 128.24 (12) | H7A—C7—H7B | 114.7 (17) |
O2—C5—C6 | 109.31 (12) | O1—C8—H8 | 116.7 (13) |
C4—C5—C6 | 122.43 (12) | C1—C8—H8 | 119.1 (13) |
| | | |
C7—O2—C5—C4 | −175.63 (14) | C8—C1—C6—O3 | −1.6 (2) |
C7—O2—C5—C6 | 6.14 (14) | C8—C1—C6—C5 | −178.66 (13) |
C5—O2—C7—O3 | −10.25 (14) | C2—C1—C8—O1 | −1.3 (2) |
C7—O3—C6—C1 | 175.65 (13) | C6—C1—C8—O1 | 177.54 (14) |
C7—O3—C6—C5 | −7.00 (14) | C1—C2—C3—N1 | 179.31 (12) |
C6—O3—C7—O2 | 10.61 (14) | C1—C2—C3—C4 | −0.5 (2) |
O4—N1—C3—C2 | 8.8 (2) | N1—C3—C4—C5 | −179.31 (12) |
O4—N1—C3—C4 | −171.40 (14) | C2—C3—C4—C5 | 0.5 (2) |
O5—N1—C3—C2 | −170.89 (13) | C3—C4—C5—O2 | −178.15 (13) |
O5—N1—C3—C4 | 8.95 (19) | C3—C4—C5—C6 | −0.13 (19) |
C6—C1—C2—C3 | 0.1 (2) | O2—C5—C6—O3 | 0.58 (15) |
C8—C1—C2—C3 | 179.02 (13) | O2—C5—C6—C1 | 178.10 (12) |
C2—C1—C6—O3 | 177.32 (13) | C4—C5—C6—O3 | −177.77 (12) |
C2—C1—C6—C5 | 0.25 (19) | C4—C5—C6—C1 | −0.3 (2) |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+2, y+1/2, −z+1/2; (iii) −x+1, −y+2, −z; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+3/2, z+1/2; (vi) x+1, y, z; (vii) x, −y+3/2, z−1/2; (viii) x+1, −y+3/2, z−1/2; (ix) x−1, y, z; (x) x−1, −y+3/2, z+1/2; (xi) −x+2, y−1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O1iv | 0.95 (2) | 2.401 (19) | 3.2531 (18) | 148.8 (17) |
C7—H7A···O1xi | 1.01 (2) | 2.55 (2) | 3.334 (2) | 133.9 (15) |
C7—H7B···O4iv | 1.00 (2) | 2.55 (2) | 3.146 (2) | 118.1 (15) |
C7—H7B···O5viii | 1.00 (2) | 2.55 (2) | 2.991 (2) | 106.4 (14) |
Symmetry codes: (iv) −x+1, y−1/2, −z+1/2; (viii) x+1, −y+3/2, z−1/2; (xi) −x+2, y−1/2, −z+1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.