Download citation
Download citation
link to html
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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804007500/hg6030sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804007500/hg6030Isup2.hkl
Contains datablock I

CCDC reference: 239121

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](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
C10H10N2O4F(000) = 232
Mr = 222.2Dx = 1.351 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -p_2ybcCell parameters from 1359 reflections
a = 10.503 (7) Åθ = 2.8–27.0°
b = 4.436 (3) ŵ = 0.11 mm1
c = 12.571 (8) ÅT = 150 K
β = 111.161 (8)°Lath, colourless
V = 546.2 (6) Å30.65 × 0.15 × 0.03 mm
Z = 2
Data collection top
Bruker SMART CCD
diffractometer
1281 independent reflections
Radiation source: sealed tube913 reflections with I > 2σ(I)'
Graphite monochromatorRint = 0.043
ω scansθmax = 28.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.814, Tmax = 0.999k = 55
4840 measured reflectionsl = 1615
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: difference Fourier map
wR(F2) = 0.142All H-atom parameters refined
S = 1.10 w = 1/[σ2(F2) + 1.2F2 + .0005F4]
1281 reflections(Δ/σ)max = 0.011
93 parametersΔρmax = 0.43 e Å3
1 restraintΔρmin = 0.33 e Å3
0 constraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0591 (2)0.5078 (5)0.49076 (18)0.0253 (10)
C110.1685 (2)0.7092 (6)0.5543 (2)0.0288 (11)
N110.2600 (2)0.8615 (6)0.5989 (2)0.0380 (11)
C20.0874 (2)0.3113 (5)0.40239 (19)0.0266 (10)
O20.00791 (18)0.1240 (4)0.34776 (14)0.0328 (8)
O30.20825 (17)0.3745 (4)0.39865 (14)0.0298 (8)
C30.2516 (3)0.1877 (6)0.3211 (2)0.0324 (12)
C40.3999 (3)0.2521 (8)0.3479 (3)0.0418 (15)
H3a0.189 (3)0.245 (7)0.242 (2)0.031 (7)*
H3b0.232 (3)0.029 (8)0.333 (2)0.041 (8)*
H4a0.434 (4)0.132 (9)0.299 (3)0.065 (11)*
H4b0.457 (3)0.196 (8)0.424 (3)0.060 (10)*
H4c0.415 (3)0.470 (9)0.337 (3)0.054 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0356 (12)0.0214 (11)0.0214 (10)0.0006 (10)0.0133 (9)0.0028 (9)
C110.0352 (13)0.0315 (13)0.0250 (11)0.0007 (11)0.0172 (10)0.0009 (10)
N110.0394 (12)0.0429 (14)0.0363 (11)0.0055 (11)0.0192 (10)0.0067 (10)
C20.0367 (13)0.0239 (12)0.0233 (10)0.0009 (10)0.0158 (10)0.0026 (9)
O20.0401 (10)0.0313 (10)0.0326 (9)0.0056 (8)0.0198 (8)0.0070 (8)
O30.0386 (10)0.0288 (9)0.0298 (8)0.0006 (7)0.0218 (8)0.0024 (7)
C30.0429 (15)0.0319 (14)0.0317 (13)0.0022 (11)0.0248 (12)0.0029 (11)
C40.0446 (16)0.048 (2)0.0390 (15)0.0067 (14)0.0226 (13)0.0018 (14)
Geometric parameters (Å, º) top
C1—C111.447 (3)C3—C41.498 (4)
C1—C21.523 (4)C3—H3a1.00 (2)
C1—C11.344 (4)C3—H3b1.01 (3)
C11—N111.143 (3)C4—H4a0.98 (4)
C2—O21.202 (3)C4—H4b0.96 (3)
C2—O31.318 (3)C4—H4c0.99 (4)
O3—C31.471 (4)
C11—C1—C2115.5 (2)O3—C3—H3b108 (2)
C11—C1—C1122.3 (2)C4—C3—H3a115.5 (18)
C2—C1—C1122.2 (2)C4—C3—H3b113.4 (17)
C1—C11—N11174.6 (3)H3a—C3—H3b107 (2)
C1—C2—O2122.3 (3)C3—C4—H4a110 (2)
C1—C2—O3110.4 (2)C3—C4—H4b113 (2)
O2—C2—O3127.3 (3)C3—C4—H4c111 (2)
C2—O3—C3115.88 (19)H4a—C4—H4b105 (3)
O3—C3—C4106.8 (2)H4a—C4—H4c109 (3)
O3—C3—H3a105.1 (18)H4b—C4—H4c109 (3)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds