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The title compound, C6H7NO2, was synthesized from cis-1,2-cyclo­butane­dicarboxylic anhydride by reaction with ammonium acetate under microwave conditions. The crystal structure of the compound shows that the cyclo­butane ring is planar with angles ranging from 89.64 (12) to 90.37 (12)°. The cis-3-aza­bicyclo­[3.2.0]heptane-2,4-dione mol­ecules are linked into a chain formation through hydrogen N—H...O=C bonds. Parallel packing is seen between two cyclo­butane rings related by inversion symmetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806006933/sj2009sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806006933/sj2009Isup2.hkl
Contains datablock I

CCDC reference: 605177

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.049
  • wR factor = 0.134
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT057_ALERT_3_C Correction for Absorption Required RT(exp) ... 1.12 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
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 2 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL (Bruker, 1999).

cis-3-Azabicyclo[3.2.0]heptane-2,4-dione top
Crystal data top
C6H7NO2F(000) = 264
Mr = 125.13Dx = 1.409 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 9.4771 (5) ÅCell parameters from 79 reflections
b = 7.6956 (5) Åθ = 2.5–27.9°
c = 8.3279 (5) ŵ = 0.90 mm1
β = 103.763 (4)°T = 293 K
V = 589.93 (6) Å3Chunk, colorless
Z = 40.58 × 0.55 × 0.40 mm
Data collection top
Bruker P4
diffractometer
Rint = 0.079
Radiation source: fine-focus sealed tubeθmax = 69.0°, θmin = 4.8°
Graphite monochromatorh = 1111
2θ/ω scansk = 09
1319 measured reflectionsl = 1010
1081 independent reflections3 standard reflections every 97 reflections
1008 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.134 w = 1/[σ2(Fo2) + (0.0725P)2 + 0.1848P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
1081 reflectionsΔρmax = 0.23 e Å3
83 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.078 (12)
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
xyzUiso*/Ueq
O10.50754 (15)0.45880 (17)0.2894 (2)0.0671 (6)
O20.84373 (14)0.15003 (17)0.10039 (18)0.0602 (5)
N0.65817 (15)0.27456 (17)0.19275 (18)0.0438 (5)
H2B0.60130.18590.17790.053*
C10.62272 (18)0.4310 (2)0.2542 (2)0.0435 (5)
C20.74626 (18)0.5536 (2)0.26244 (19)0.0407 (5)
H2A0.78360.60760.37080.049*
C30.7265 (2)0.6799 (2)0.1142 (2)0.0518 (5)
H3A0.62950.67840.04240.062*
H3B0.75720.79790.14560.062*
C40.8375 (2)0.5756 (2)0.0472 (2)0.0501 (5)
H4A0.92410.64100.04320.060*
H4B0.79670.51980.05810.060*
C50.85891 (16)0.4502 (2)0.19739 (19)0.0399 (5)
H5A0.95690.45010.27000.048*
C60.79288 (17)0.2736 (2)0.15738 (19)0.0399 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0669 (9)0.0389 (8)0.1108 (13)0.0064 (6)0.0518 (9)0.0041 (7)
O20.0627 (9)0.0392 (7)0.0801 (10)0.0126 (6)0.0197 (7)0.0110 (6)
N0.0440 (8)0.0246 (7)0.0630 (9)0.0025 (5)0.0133 (6)0.0030 (6)
C10.0534 (10)0.0278 (8)0.0539 (10)0.0035 (7)0.0218 (7)0.0028 (6)
C20.0567 (10)0.0284 (8)0.0396 (8)0.0038 (6)0.0167 (7)0.0037 (6)
C30.0674 (12)0.0342 (9)0.0607 (10)0.0063 (7)0.0289 (9)0.0112 (7)
C40.0656 (11)0.0394 (9)0.0517 (10)0.0018 (8)0.0264 (8)0.0035 (7)
C50.0375 (8)0.0345 (8)0.0461 (8)0.0006 (6)0.0068 (6)0.0006 (6)
C60.0420 (9)0.0308 (8)0.0445 (8)0.0061 (6)0.0055 (6)0.0002 (6)
Geometric parameters (Å, º) top
O1—C11.2146 (19)C3—C41.531 (2)
O2—C61.213 (2)C3—H3A0.9700
N—C61.377 (2)C3—H3B0.9700
N—C11.380 (2)C4—C51.554 (2)
N—H2B0.8600C4—H4A0.9700
C1—C21.493 (2)C4—H4B0.9700
C2—C51.530 (2)C5—C61.500 (2)
C2—C31.547 (2)C5—H5A0.9800
C2—H2A0.9800
C6—N—C1113.81 (13)H3A—C3—H3B110.9
C6—N—H2B123.1C3—C4—C590.10 (12)
C1—N—H2B123.1C3—C4—H4A113.6
O1—C1—N123.72 (15)C5—C4—H4A113.6
O1—C1—C2128.14 (15)C3—C4—H4B113.6
N—C1—C2108.11 (13)C5—C4—H4B113.6
C1—C2—C5105.12 (13)H4A—C4—H4B110.9
C1—C2—C3114.58 (15)C6—C5—C2105.09 (12)
C5—C2—C390.37 (12)C6—C5—C4114.57 (14)
C1—C2—H2A114.7C2—C5—C489.64 (12)
C5—C2—H2A114.7C6—C5—H5A114.8
C3—C2—H2A114.7C2—C5—H5A114.8
C4—C3—C289.88 (12)C4—C5—H5A114.8
C4—C3—H3A113.7O2—C6—N124.25 (16)
C2—C3—H3A113.7O2—C6—C5127.86 (16)
C4—C3—H3B113.7N—C6—C5107.87 (13)
C2—C3—H3B113.7
C6—N—C1—O1178.34 (16)C1—C2—C5—C4114.90 (14)
C6—N—C1—C20.17 (19)C3—C2—C5—C40.74 (13)
O1—C1—C2—C5177.83 (17)C3—C4—C5—C6107.21 (15)
N—C1—C2—C50.24 (18)C3—C4—C5—C20.74 (13)
O1—C1—C2—C380.3 (2)C1—N—C6—O2178.99 (15)
N—C1—C2—C397.76 (16)C1—N—C6—C50.51 (18)
C1—C2—C3—C4106.10 (16)C2—C5—C6—O2179.03 (16)
C5—C2—C3—C40.75 (14)C4—C5—C6—O282.4 (2)
C2—C3—C4—C50.74 (13)C2—C5—C6—N0.62 (16)
C1—C2—C5—C60.51 (16)C4—C5—C6—N96.05 (16)
C3—C2—C5—C6116.14 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H2B···O1i0.862.082.9163 (19)164
Symmetry code: (i) x+1, y1/2, z+1/2.
 

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