organic compounds
In the title planar centrosymmetric molecule, C10H10N2O4, multiple-bond character remains essentially localized: C-O/N = 1.202 (3) and 1.143 (3) Å, and central C=C 1.344 (4) Å.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804007500/hg6030sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804007500/hg6030Isup2.hkl |
CCDC reference: 239121
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.004 Å
- R factor = 0.085
- wR factor = 0.142
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.814 0.999 Tmin' and Tmax expected: 0.933 0.997 RR' = 0.871 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.87 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C11 ... 1.45 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 0 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 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: Xtal3.5 (Hall et al., 1995); program(s) used to refine structure: Xtal3.5 CRYLSQ; molecular graphics: Xtal3.5; software used to prepare material for publication: Xtal3.5 CIFIO.
(I) top
Crystal data top
C10H10N2O4 | F(000) = 232 |
Mr = 222.2 | Dx = 1.351 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p_2ybc | Cell parameters from 1359 reflections |
a = 10.503 (7) Å | θ = 2.8–27.0° |
b = 4.436 (3) Å | µ = 0.11 mm−1 |
c = 12.571 (8) Å | T = 150 K |
β = 111.161 (8)° | Lath, colourless |
V = 546.2 (6) Å3 | 0.65 × 0.15 × 0.03 mm |
Z = 2 |
Data collection top
Bruker SMART CCD diffractometer | 1281 independent reflections |
Radiation source: sealed tube | 913 reflections with I > 2σ(I)' |
Graphite monochromator | Rint = 0.043 |
ω scans | θmax = 28.5°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.814, Tmax = 0.999 | k = −5→5 |
4840 measured reflections | l = −16→15 |
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)] = 0.055 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.142 | All H-atom parameters refined |
S = 1.10 | w = 1/[σ2(F2) + 1.2F2 + .0005F4] |
1281 reflections | (Δ/σ)max = 0.011 |
93 parameters | Δρmax = 0.43 e Å−3 |
1 restraint | Δρmin = −0.33 e Å−3 |
0 constraints |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1 | 0.0591 (2) | 0.5078 (5) | 0.49076 (18) | 0.0253 (10) | |
C11 | 0.1685 (2) | 0.7092 (6) | 0.5543 (2) | 0.0288 (11) | |
N11 | 0.2600 (2) | 0.8615 (6) | 0.5989 (2) | 0.0380 (11) | |
C2 | 0.0874 (2) | 0.3113 (5) | 0.40239 (19) | 0.0266 (10) | |
O2 | 0.00791 (18) | 0.1240 (4) | 0.34776 (14) | 0.0328 (8) | |
O3 | 0.20825 (17) | 0.3745 (4) | 0.39865 (14) | 0.0298 (8) | |
C3 | 0.2516 (3) | 0.1877 (6) | 0.3211 (2) | 0.0324 (12) | |
C4 | 0.3999 (3) | 0.2521 (8) | 0.3479 (3) | 0.0418 (15) | |
H3a | 0.189 (3) | 0.245 (7) | 0.242 (2) | 0.031 (7)* | |
H3b | 0.232 (3) | −0.029 (8) | 0.333 (2) | 0.041 (8)* | |
H4a | 0.434 (4) | 0.132 (9) | 0.299 (3) | 0.065 (11)* | |
H4b | 0.457 (3) | 0.196 (8) | 0.424 (3) | 0.060 (10)* | |
H4c | 0.415 (3) | 0.470 (9) | 0.337 (3) | 0.054 (10)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0356 (12) | 0.0214 (11) | 0.0214 (10) | 0.0006 (10) | 0.0133 (9) | 0.0028 (9) |
C11 | 0.0352 (13) | 0.0315 (13) | 0.0250 (11) | 0.0007 (11) | 0.0172 (10) | 0.0009 (10) |
N11 | 0.0394 (12) | 0.0429 (14) | 0.0363 (11) | −0.0055 (11) | 0.0192 (10) | −0.0067 (10) |
C2 | 0.0367 (13) | 0.0239 (12) | 0.0233 (10) | 0.0009 (10) | 0.0158 (10) | 0.0026 (9) |
O2 | 0.0401 (10) | 0.0313 (10) | 0.0326 (9) | −0.0056 (8) | 0.0198 (8) | −0.0070 (8) |
O3 | 0.0386 (10) | 0.0288 (9) | 0.0298 (8) | −0.0006 (7) | 0.0218 (8) | −0.0024 (7) |
C3 | 0.0429 (15) | 0.0319 (14) | 0.0317 (13) | 0.0022 (11) | 0.0248 (12) | −0.0029 (11) |
C4 | 0.0446 (16) | 0.048 (2) | 0.0390 (15) | 0.0067 (14) | 0.0226 (13) | 0.0018 (14) |
Geometric parameters (Å, º) top
C1—C11 | 1.447 (3) | C3—C4 | 1.498 (4) |
C1—C2 | 1.523 (4) | C3—H3a | 1.00 (2) |
C1—C1 | 1.344 (4) | C3—H3b | 1.01 (3) |
C11—N11 | 1.143 (3) | C4—H4a | 0.98 (4) |
C2—O2 | 1.202 (3) | C4—H4b | 0.96 (3) |
C2—O3 | 1.318 (3) | C4—H4c | 0.99 (4) |
O3—C3 | 1.471 (4) | ||
C11—C1—C2 | 115.5 (2) | O3—C3—H3b | 108 (2) |
C11—C1—C1 | 122.3 (2) | C4—C3—H3a | 115.5 (18) |
C2—C1—C1 | 122.2 (2) | C4—C3—H3b | 113.4 (17) |
C1—C11—N11 | 174.6 (3) | H3a—C3—H3b | 107 (2) |
C1—C2—O2 | 122.3 (3) | C3—C4—H4a | 110 (2) |
C1—C2—O3 | 110.4 (2) | C3—C4—H4b | 113 (2) |
O2—C2—O3 | 127.3 (3) | C3—C4—H4c | 111 (2) |
C2—O3—C3 | 115.88 (19) | H4a—C4—H4b | 105 (3) |
O3—C3—C4 | 106.8 (2) | H4a—C4—H4c | 109 (3) |
O3—C3—H3a | 105.1 (18) | H4b—C4—H4c | 109 (3) |