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The reaction of cyclo­hexa­necarboxaldehyde with 1-aza­bicylo[2.2.2]octan-3-one in methano­lic KOH afforded the title compound, C14H21NO. The cyclo­hexane ring adopts a chair conformation and the olefinic double bond has Z geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047453/lh2243sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047453/lh2243Isup2.hkl
Contains datablock I

CCDC reference: 630163

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.031
  • wR factor = 0.077
  • Data-to-parameter ratio = 10.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
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 27.48 From the CIF: _reflns_number_total 1498 Count of symmetry unique reflns 1503 Completeness (_total/calc) 99.67% 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 1 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO–SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1995); software used to prepare material for publication: SHELX97-2 (Sheldrick, 1997) and local procedures.

(Z)-2-(Cyclohexylidene)-1-azabicyclo[2.2.2]octan-3-one top
Crystal data top
C14H21NOF(000) = 240
Mr = 219.32Dx = 1.201 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1487 reflections
a = 9.2795 (2) Åθ = 1.0–27.5°
b = 6.7778 (1) ŵ = 0.08 mm1
c = 9.8401 (2) ÅT = 90 K
β = 101.5236 (9)°Cut block, colourless
V = 606.41 (2) Å30.40 × 0.30 × 0.25 mm
Z = 2
Data collection top
Nonius KappaCCD
diffractometer
1498 independent reflections
Radiation source: fine-focus sealed tube1437 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
Detector resolution: 18 pixels mm-1θmax = 27.5°, θmin = 2.1°
ω scans at fixed χ = 55°h = 1112
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
k = 88
Tmin = 0.971, Tmax = 0.982l = 1212
2756 measured reflections
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0399P)2 + 0.135P]
where P = (Fo2 + 2Fc2)/3
1498 reflections(Δ/σ)max = 0.001
145 parametersΔρmax = 0.23 e Å3
1 restraintΔρmin = 0.15 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
N10.03323 (13)0.3239 (2)0.67491 (13)0.0168 (3)
O10.12395 (13)0.1092 (2)1.01770 (11)0.0259 (3)
C10.31202 (15)0.5485 (2)0.77116 (15)0.0167 (3)
H10.23150.60050.69680.020*
C20.42560 (17)0.4448 (2)0.70103 (17)0.0208 (3)
H2A0.50310.38450.77280.025*
H2B0.37670.33800.64010.025*
C30.49587 (17)0.5909 (3)0.61509 (16)0.0217 (3)
H3A0.57180.52220.57490.026*
H3B0.41980.64120.53760.026*
C40.56605 (17)0.7637 (3)0.70327 (17)0.0233 (4)
H4A0.64850.71510.77540.028*
H4B0.60620.85880.64410.028*
C50.45413 (18)0.8672 (3)0.77210 (17)0.0231 (4)
H5A0.37710.92760.70000.028*
H5B0.50340.97410.83260.028*
C60.38279 (17)0.7232 (3)0.85852 (16)0.0213 (3)
H6A0.30680.79340.89770.026*
H6B0.45830.67370.93670.026*
C70.24625 (16)0.4029 (2)0.85586 (15)0.0179 (3)
H70.29750.38010.94820.021*
C80.12236 (16)0.3030 (2)0.81294 (15)0.0159 (3)
C90.02946 (18)0.1295 (3)0.60546 (16)0.0219 (4)
H9A0.13030.09320.59610.026*
H9B0.03200.13940.51110.026*
C100.03310 (18)0.0344 (3)0.68690 (17)0.0220 (3)
H10A0.12170.09330.62820.026*
H10B0.04100.13990.71320.026*
C110.07289 (16)0.0569 (2)0.81812 (16)0.0190 (3)
H110.11190.04510.87480.023*
C120.06546 (17)0.1513 (2)0.89894 (16)0.0180 (3)
C130.18536 (16)0.2235 (3)0.77418 (16)0.0191 (3)
H13A0.20900.28790.85740.023*
H13B0.27730.16860.71850.023*
C140.11873 (16)0.3764 (3)0.68726 (16)0.0191 (3)
H14A0.18140.38480.59340.023*
H14B0.11810.50780.73130.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0164 (6)0.0199 (7)0.0134 (6)0.0022 (5)0.0015 (4)0.0001 (5)
O10.0301 (6)0.0271 (7)0.0182 (5)0.0032 (5)0.0005 (4)0.0068 (5)
C10.0163 (7)0.0162 (8)0.0171 (7)0.0019 (6)0.0015 (5)0.0006 (6)
C20.0228 (7)0.0162 (8)0.0244 (8)0.0005 (6)0.0069 (6)0.0011 (7)
C30.0200 (7)0.0231 (8)0.0229 (8)0.0014 (7)0.0067 (6)0.0001 (7)
C40.0194 (7)0.0250 (9)0.0244 (8)0.0058 (7)0.0017 (6)0.0043 (7)
C50.0286 (8)0.0167 (8)0.0223 (8)0.0053 (7)0.0012 (6)0.0005 (7)
C60.0240 (8)0.0190 (8)0.0207 (8)0.0034 (7)0.0041 (6)0.0022 (7)
C70.0183 (7)0.0188 (8)0.0157 (7)0.0012 (6)0.0014 (5)0.0012 (6)
C80.0159 (7)0.0163 (7)0.0155 (7)0.0009 (6)0.0028 (5)0.0011 (6)
C90.0220 (8)0.0262 (9)0.0179 (7)0.0025 (7)0.0052 (6)0.0052 (7)
C100.0219 (7)0.0190 (8)0.0247 (8)0.0015 (7)0.0037 (6)0.0044 (7)
C110.0221 (7)0.0157 (8)0.0200 (7)0.0036 (6)0.0059 (6)0.0008 (6)
C120.0207 (7)0.0158 (7)0.0178 (7)0.0000 (6)0.0047 (6)0.0016 (6)
C130.0175 (7)0.0199 (8)0.0208 (7)0.0026 (6)0.0059 (6)0.0023 (6)
C140.0167 (7)0.0193 (8)0.0208 (7)0.0007 (6)0.0025 (5)0.0023 (7)
Geometric parameters (Å, º) top
N1—C81.4492 (18)C6—H6A0.9900
N1—C91.481 (2)C6—H6B0.9900
N1—C141.4826 (19)C7—C81.328 (2)
O1—C121.2200 (19)C7—H70.9500
C1—C71.498 (2)C8—C121.494 (2)
C1—C61.532 (2)C9—C101.549 (2)
C1—C21.540 (2)C9—H9A0.9900
C1—H11.0000C9—H9B0.9900
C2—C31.530 (2)C10—C111.542 (2)
C2—H2A0.9900C10—H10A0.9900
C2—H2B0.9900C10—H10B0.9900
C3—C41.524 (2)C11—C121.511 (2)
C3—H3A0.9900C11—C131.540 (2)
C3—H3B0.9900C11—H111.0000
C4—C51.520 (2)C13—C141.549 (2)
C4—H4A0.9900C13—H13A0.9900
C4—H4B0.9900C13—H13B0.9900
C5—C61.529 (2)C14—H14A0.9900
C5—H5A0.9900C14—H14B0.9900
C5—H5B0.9900
C8—N1—C9107.57 (12)C8—C7—C1125.57 (13)
C8—N1—C14108.71 (11)C8—C7—H7117.2
C9—N1—C14108.42 (12)C1—C7—H7117.2
C7—C1—C6111.94 (12)C7—C8—N1122.95 (13)
C7—C1—C2109.89 (13)C7—C8—C12123.52 (13)
C6—C1—C2110.43 (12)N1—C8—C12113.46 (12)
C7—C1—H1108.2N1—C9—C10112.08 (12)
C6—C1—H1108.2N1—C9—H9A109.2
C2—C1—H1108.2C10—C9—H9A109.2
C3—C2—C1110.96 (13)N1—C9—H9B109.2
C3—C2—H2A109.4C10—C9—H9B109.2
C1—C2—H2A109.4H9A—C9—H9B107.9
C3—C2—H2B109.4C11—C10—C9108.83 (13)
C1—C2—H2B109.4C11—C10—H10A109.9
H2A—C2—H2B108.0C9—C10—H10A109.9
C4—C3—C2111.31 (13)C11—C10—H10B109.9
C4—C3—H3A109.4C9—C10—H10B109.9
C2—C3—H3A109.4H10A—C10—H10B108.3
C4—C3—H3B109.4C12—C11—C13107.09 (13)
C2—C3—H3B109.4C12—C11—C10106.88 (12)
H3A—C3—H3B108.0C13—C11—C10108.74 (12)
C5—C4—C3110.85 (13)C12—C11—H11111.3
C5—C4—H4A109.5C13—C11—H11111.3
C3—C4—H4A109.5C10—C11—H11111.3
C5—C4—H4B109.5O1—C12—C8124.32 (14)
C3—C4—H4B109.5O1—C12—C11125.01 (15)
H4A—C4—H4B108.1C8—C12—C11110.66 (12)
C4—C5—C6111.33 (14)C11—C13—C14108.84 (12)
C4—C5—H5A109.4C11—C13—H13A109.9
C6—C5—H5A109.4C14—C13—H13A109.9
C4—C5—H5B109.4C11—C13—H13B109.9
C6—C5—H5B109.4C14—C13—H13B109.9
H5A—C5—H5B108.0H13A—C13—H13B108.3
C5—C6—C1111.46 (13)N1—C14—C13112.08 (13)
C5—C6—H6A109.3N1—C14—H14A109.2
C1—C6—H6A109.3C13—C14—H14A109.2
C5—C6—H6B109.3N1—C14—H14B109.2
C1—C6—H6B109.3C13—C14—H14B109.2
H6A—C6—H6B108.0H14A—C14—H14B107.9
C7—C1—C2—C3179.34 (12)C14—N1—C9—C1059.21 (16)
C6—C1—C2—C355.37 (17)N1—C9—C10—C110.08 (18)
C1—C2—C3—C456.28 (17)C9—C10—C11—C1257.08 (17)
C2—C3—C4—C556.41 (18)C9—C10—C11—C1358.22 (16)
C3—C4—C5—C656.03 (18)C7—C8—C12—O12.5 (2)
C4—C5—C6—C155.96 (18)N1—C8—C12—O1179.55 (16)
C7—C1—C6—C5178.05 (13)C7—C8—C12—C11176.92 (15)
C2—C1—C6—C555.26 (17)N1—C8—C12—C110.08 (18)
C6—C1—C7—C8142.91 (16)C13—C11—C12—O1122.34 (17)
C2—C1—C7—C894.00 (18)C10—C11—C12—O1121.26 (18)
C1—C7—C8—N10.1 (2)C13—C11—C12—C858.20 (15)
C1—C7—C8—C12176.60 (14)C10—C11—C12—C858.20 (16)
C9—N1—C8—C7117.95 (16)C12—C11—C13—C1458.06 (15)
C14—N1—C8—C7124.84 (16)C10—C11—C13—C1457.11 (16)
C9—N1—C8—C1259.07 (15)C8—N1—C14—C1356.26 (16)
C14—N1—C8—C1258.13 (16)C9—N1—C14—C1360.40 (15)
C8—N1—C9—C1058.18 (16)C11—C13—C14—N11.84 (17)
 

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