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The title compound, C8H13NO, with two chiral centres in the cis-junction between the β-lactam and cyclo­heptane rings, crystallizes with an orthorhombic unit cell. The strain of the β-lactam moiety forces the cyclo­heptane ring to assume a chair conformation characterized by Cs symmetry, which is less stable by 1.4 kcal mol−1 than the twist-chair form, built up around a twofold axis. The homochiral helices, maintained by N—H...O=C hydrogen bonds, are organized in antiparallel mode around the respective screw axes of the non-centrosymmetric space group P212121, which means that the enantiomers resolve in crystal conglomerates.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680302796X/lh6151sup1.cif
Contains datablocks 3, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680302796X/lh61513sup2.hkl
Contains datablock 3

CCDC reference: 234856

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.066
  • wR factor = 0.227
  • Data-to-parameter ratio = 10.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 74.85 From the CIF: _reflns_number_total 941 Count of symmetry unique reflns 954 Completeness (_total/calc) 98.64% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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: CAD-4 EXPRESS (Enraf-Nonius, 1992); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and RPluto in CSD (Allen, F. H. (2002); software used to prepare material for publication: SHELXL97.

cis-8-azabicyclo[5.2.0]nonan-9-one top
Crystal data top
C8H13NODx = 1.189 Mg m3
Mr = 139.19Melting point = 328–329 K
Orthorhombic, P212121Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 6.683 (1) Åθ = 24.3–25.5°
b = 9.166 (1) ŵ = 0.62 mm1
c = 12.696 (2) ÅT = 293 K
V = 777.71 (19) Å3Prism, colourless
Z = 40.35 × 0.20 × 0.15 mm
F(000) = 304
Data collection top
Enraf-Nonius CAD4
diffractometer
842 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
Graphite monochromatorθmax = 74.9°, θmin = 6.0°
ωθ scansh = 88
Absorption correction: ψ scan
(North et al., 1968)
k = 1111
Tmin = 0.892, Tmax = 0.910l = 1515
1863 measured reflections3 standard reflections every 60 min
941 independent reflections intensity decay: 16%
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.227H-atom parameters constrained
S = 1.98 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
941 reflections(Δ/σ)max < 0.001
91 parametersΔρmax = 0.23 e Å3
86 restraintsΔρmin = 0.28 e Å3
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
C10.4015 (4)0.4291 (4)0.2136 (2)0.0546 (7)
H10.38300.53420.20330.071*
C20.4753 (4)0.3970 (4)0.3239 (2)0.0539 (7)
H2A0.50700.29400.32900.070*
H2B0.59760.45130.33610.070*
C30.3248 (5)0.4357 (4)0.4092 (2)0.0624 (9)
H3A0.39630.44930.47500.081*
H3B0.26300.52820.39120.081*
C40.1599 (6)0.3236 (5)0.4268 (3)0.0734 (10)
H4A0.07870.35580.48570.095*
H4B0.22210.23220.44710.095*
C50.0210 (5)0.2938 (5)0.3335 (3)0.0715 (10)
H5A0.04250.38470.31300.093*
H5B0.08370.22750.35610.093*
C60.1239 (5)0.2294 (4)0.2382 (3)0.0657 (9)
H6A0.22520.16090.26170.085*
H6B0.02650.17550.19700.085*
C70.2206 (5)0.3426 (4)0.1692 (2)0.0609 (8)
H70.12060.40830.13860.079*
N80.3600 (5)0.2879 (4)0.0878 (2)0.0723 (9)
H80.34380.22850.03610.094*
C90.5201 (5)0.3623 (4)0.1218 (2)0.0630 (8)
O10.6909 (4)0.3724 (4)0.0909 (2)0.0895 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0524 (15)0.0613 (15)0.0499 (14)0.0004 (13)0.0036 (11)0.0037 (11)
C20.0428 (13)0.0676 (16)0.0511 (14)0.0004 (12)0.0005 (11)0.0063 (12)
C30.0613 (19)0.0773 (19)0.0488 (13)0.0043 (15)0.0045 (14)0.0116 (14)
C40.0635 (19)0.097 (2)0.0593 (17)0.0014 (19)0.0131 (14)0.0051 (16)
C50.0472 (15)0.087 (2)0.080 (2)0.0049 (16)0.0019 (15)0.0166 (18)
C60.0565 (15)0.0700 (17)0.0705 (18)0.0115 (15)0.0135 (14)0.0045 (15)
C70.0574 (16)0.0743 (18)0.0511 (14)0.0031 (15)0.0125 (12)0.0026 (14)
N80.0811 (18)0.0895 (19)0.0464 (12)0.0014 (16)0.0085 (13)0.0136 (13)
C90.0664 (17)0.0780 (18)0.0447 (13)0.0035 (16)0.0049 (12)0.0052 (13)
O10.0736 (17)0.125 (2)0.0703 (15)0.0044 (17)0.0238 (14)0.0227 (16)
Geometric parameters (Å, º) top
C1—C21.513 (4)C4—H4B0.9700
C1—C71.552 (4)C5—C61.511 (5)
C1—C91.537 (4)C5—H5A0.9700
C1—H10.9800C5—H5B0.9700
C2—C31.521 (4)C6—C71.505 (5)
C2—H2A0.9700C6—H6A0.9700
C2—H2B0.9700C6—H6B0.9700
C3—C41.524 (5)C7—N81.478 (4)
C3—H3A0.9700C7—H70.9800
C3—H3B0.9700N8—C91.340 (5)
C4—C51.530 (5)N8—H80.8600
C4—H4A0.9700C9—O11.210 (4)
C2—C1—C7119.4 (3)C4—C5—C6114.4 (3)
C2—C1—C9117.1 (2)C4—C5—H5A108.7
C7—C1—C985.6 (2)C6—C5—H5A108.7
C2—C1—H1110.8C4—C5—H5B108.7
C7—C1—H1110.8C6—C5—H5B108.7
C9—C1—H1110.8H5A—C5—H5B107.6
C3—C2—C1113.5 (2)C7—C6—C5113.1 (3)
C3—C2—H2A108.9C7—C6—H6A109.0
C1—C2—H2A108.9C5—C6—H6A109.0
C3—C2—H2B108.9C7—C6—H6B109.0
C1—C2—H2B108.9C5—C6—H6B109.0
H2A—C2—H2B107.7H6A—C6—H6B107.8
C4—C3—C2115.2 (3)N8—C7—C6116.4 (3)
C4—C3—H3A108.5N8—C7—C186.3 (2)
C2—C3—H3A108.5C6—C7—C1118.4 (2)
C4—C3—H3B108.5N8—C7—H7111.2
C2—C3—H3B108.5C6—C7—H7111.2
H3A—C3—H3B107.5C1—C7—H7111.2
C3—C4—C5116.4 (3)C9—N8—C796.1 (2)
C3—C4—H4A108.2C9—N8—H8132.0
C5—C4—H4A108.2C7—N8—H8132.0
C3—C4—H4B108.2O1—C9—N8133.4 (3)
C5—C4—H4B108.2O1—C9—C1134.6 (3)
H4A—C4—H4B107.3N8—C9—C192.0 (2)
C7—C1—C2—C365.4 (4)C2—C1—C7—C60.3 (4)
C9—C1—C2—C3166.3 (3)C9—C1—C7—C6119.0 (3)
C1—C2—C3—C480.4 (4)C6—C7—N8—C9121.0 (3)
C2—C3—C4—C561.9 (4)C1—C7—N8—C91.0 (3)
C3—C4—C5—C663.3 (4)C7—N8—C9—O1178.6 (5)
C4—C5—C6—C783.5 (4)C7—N8—C9—C11.0 (3)
C5—C6—C7—N8167.3 (3)C2—C1—C9—O160.5 (6)
C5—C6—C7—C166.5 (4)C7—C1—C9—O1178.7 (5)
C2—C1—C7—N8117.9 (3)C2—C1—C9—N8119.9 (3)
C9—C1—C7—N80.9 (2)C7—C1—C9—N81.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8—H8···O1i0.862.122.929 (4)157
Symmetry code: (i) x1/2, y+1/2, z.
 

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