The title compound, C
6H
7NO
2, 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
CCDC reference: 605177
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C6H7NO2 | F(000) = 264 |
Mr = 125.13 | Dx = 1.409 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 9.4771 (5) Å | Cell parameters from 79 reflections |
b = 7.6956 (5) Å | θ = 2.5–27.9° |
c = 8.3279 (5) Å | µ = 0.90 mm−1 |
β = 103.763 (4)° | T = 293 K |
V = 589.93 (6) Å3 | Chunk, colorless |
Z = 4 | 0.58 × 0.55 × 0.40 mm |
Data collection top
Bruker P4 diffractometer | Rint = 0.079 |
Radiation source: fine-focus sealed tube | θmax = 69.0°, θmin = 4.8° |
Graphite monochromator | h = −11→11 |
2θ/ω scans | k = 0→9 |
1319 measured reflections | l = −10→10 |
1081 independent reflections | 3 standard reflections every 97 reflections |
1008 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.049 | H-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 reflections | Δρmax = 0.23 e Å−3 |
83 parameters | Δρmin = −0.19 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: 0.078 (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 | x | y | z | Uiso*/Ueq | |
O1 | 0.50754 (15) | 0.45880 (17) | 0.2894 (2) | 0.0671 (6) | |
O2 | 0.84373 (14) | 0.15003 (17) | 0.10039 (18) | 0.0602 (5) | |
N | 0.65817 (15) | 0.27456 (17) | 0.19275 (18) | 0.0438 (5) | |
H2B | 0.6013 | 0.1859 | 0.1779 | 0.053* | |
C1 | 0.62272 (18) | 0.4310 (2) | 0.2542 (2) | 0.0435 (5) | |
C2 | 0.74626 (18) | 0.5536 (2) | 0.26244 (19) | 0.0407 (5) | |
H2A | 0.7836 | 0.6076 | 0.3708 | 0.049* | |
C3 | 0.7265 (2) | 0.6799 (2) | 0.1142 (2) | 0.0518 (5) | |
H3A | 0.6295 | 0.6784 | 0.0424 | 0.062* | |
H3B | 0.7572 | 0.7979 | 0.1456 | 0.062* | |
C4 | 0.8375 (2) | 0.5756 (2) | 0.0472 (2) | 0.0501 (5) | |
H4A | 0.9241 | 0.6410 | 0.0432 | 0.060* | |
H4B | 0.7967 | 0.5198 | −0.0581 | 0.060* | |
C5 | 0.85891 (16) | 0.4502 (2) | 0.19739 (19) | 0.0399 (5) | |
H5A | 0.9569 | 0.4501 | 0.2700 | 0.048* | |
C6 | 0.79288 (17) | 0.2736 (2) | 0.15738 (19) | 0.0399 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0669 (9) | 0.0389 (8) | 0.1108 (13) | 0.0064 (6) | 0.0518 (9) | 0.0041 (7) |
O2 | 0.0627 (9) | 0.0392 (7) | 0.0801 (10) | 0.0126 (6) | 0.0197 (7) | −0.0110 (6) |
N | 0.0440 (8) | 0.0246 (7) | 0.0630 (9) | −0.0025 (5) | 0.0133 (6) | −0.0030 (6) |
C1 | 0.0534 (10) | 0.0278 (8) | 0.0539 (10) | 0.0035 (7) | 0.0218 (7) | 0.0028 (6) |
C2 | 0.0567 (10) | 0.0284 (8) | 0.0396 (8) | −0.0038 (6) | 0.0167 (7) | −0.0037 (6) |
C3 | 0.0674 (12) | 0.0342 (9) | 0.0607 (10) | 0.0063 (7) | 0.0289 (9) | 0.0112 (7) |
C4 | 0.0656 (11) | 0.0394 (9) | 0.0517 (10) | 0.0018 (8) | 0.0264 (8) | 0.0035 (7) |
C5 | 0.0375 (8) | 0.0345 (8) | 0.0461 (8) | −0.0006 (6) | 0.0068 (6) | 0.0006 (6) |
C6 | 0.0420 (9) | 0.0308 (8) | 0.0445 (8) | 0.0061 (6) | 0.0055 (6) | 0.0002 (6) |
Geometric parameters (Å, º) top
O1—C1 | 1.2146 (19) | C3—C4 | 1.531 (2) |
O2—C6 | 1.213 (2) | C3—H3A | 0.9700 |
N—C6 | 1.377 (2) | C3—H3B | 0.9700 |
N—C1 | 1.380 (2) | C4—C5 | 1.554 (2) |
N—H2B | 0.8600 | C4—H4A | 0.9700 |
C1—C2 | 1.493 (2) | C4—H4B | 0.9700 |
C2—C5 | 1.530 (2) | C5—C6 | 1.500 (2) |
C2—C3 | 1.547 (2) | C5—H5A | 0.9800 |
C2—H2A | 0.9800 | | |
| | | |
C6—N—C1 | 113.81 (13) | H3A—C3—H3B | 110.9 |
C6—N—H2B | 123.1 | C3—C4—C5 | 90.10 (12) |
C1—N—H2B | 123.1 | C3—C4—H4A | 113.6 |
O1—C1—N | 123.72 (15) | C5—C4—H4A | 113.6 |
O1—C1—C2 | 128.14 (15) | C3—C4—H4B | 113.6 |
N—C1—C2 | 108.11 (13) | C5—C4—H4B | 113.6 |
C1—C2—C5 | 105.12 (13) | H4A—C4—H4B | 110.9 |
C1—C2—C3 | 114.58 (15) | C6—C5—C2 | 105.09 (12) |
C5—C2—C3 | 90.37 (12) | C6—C5—C4 | 114.57 (14) |
C1—C2—H2A | 114.7 | C2—C5—C4 | 89.64 (12) |
C5—C2—H2A | 114.7 | C6—C5—H5A | 114.8 |
C3—C2—H2A | 114.7 | C2—C5—H5A | 114.8 |
C4—C3—C2 | 89.88 (12) | C4—C5—H5A | 114.8 |
C4—C3—H3A | 113.7 | O2—C6—N | 124.25 (16) |
C2—C3—H3A | 113.7 | O2—C6—C5 | 127.86 (16) |
C4—C3—H3B | 113.7 | N—C6—C5 | 107.87 (13) |
C2—C3—H3B | 113.7 | | |
| | | |
C6—N—C1—O1 | 178.34 (16) | C1—C2—C5—C4 | 114.90 (14) |
C6—N—C1—C2 | 0.17 (19) | C3—C2—C5—C4 | −0.74 (13) |
O1—C1—C2—C5 | −177.83 (17) | C3—C4—C5—C6 | 107.21 (15) |
N—C1—C2—C5 | 0.24 (18) | C3—C4—C5—C2 | 0.74 (13) |
O1—C1—C2—C3 | −80.3 (2) | C1—N—C6—O2 | −178.99 (15) |
N—C1—C2—C3 | 97.76 (16) | C1—N—C6—C5 | −0.51 (18) |
C1—C2—C3—C4 | −106.10 (16) | C2—C5—C6—O2 | 179.03 (16) |
C5—C2—C3—C4 | 0.75 (14) | C4—C5—C6—O2 | 82.4 (2) |
C2—C3—C4—C5 | −0.74 (13) | C2—C5—C6—N | 0.62 (16) |
C1—C2—C5—C6 | −0.51 (16) | C4—C5—C6—N | −96.05 (16) |
C3—C2—C5—C6 | −116.14 (14) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N—H2B···O1i | 0.86 | 2.08 | 2.9163 (19) | 164 |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |