(Z)-2-(Cyclo­hexyl­idene)-1-aza­bicyclo­[2.2.2]octan-3-one

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.

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

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Computing details

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

Crystal data

C14H21NO	F(000) = 240
Mr = 219.32	Dx = 1.201 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1487 reflections
a = 9.2795 (2) Å	θ = 1.0–27.5°
b = 6.7778 (1) Å	µ = 0.08 mm^−1
c = 9.8401 (2) Å	T = 90 K
β = 101.5236 (9)°	Cut block, colourless
V = 606.41 (2) Å^3	0.40 × 0.30 × 0.25 mm
Z = 2

Data collection

Nonius KappaCCD diffractometer	1498 independent reflections
Radiation source: fine-focus sealed tube	1437 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
Detector resolution: 18 pixels mm^-1	θmax = 27.5°, θmin = 2.1°
ω scans at fixed χ = 55°	h = −11→12
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −8→8
Tmin = 0.971, Tmax = 0.982	l = −12→12
2756 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.077	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0399P)^2 + 0.135P] where P = (Fo^2 + 2Fc^2)/3
1498 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.23 e Å^−3
1 restraint	Δρmin = −0.15 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.03323 (13)	0.3239 (2)	0.67491 (13)	0.0168 (3)
O1	0.12395 (13)	0.1092 (2)	1.01770 (11)	0.0259 (3)
C1	0.31202 (15)	0.5485 (2)	0.77116 (15)	0.0167 (3)
H1	0.2315	0.6005	0.6968	0.020*
C2	0.42560 (17)	0.4448 (2)	0.70103 (17)	0.0208 (3)
H2A	0.5031	0.3845	0.7728	0.025*
H2B	0.3767	0.3380	0.6401	0.025*
C3	0.49587 (17)	0.5909 (3)	0.61509 (16)	0.0217 (3)
H3A	0.5718	0.5222	0.5749	0.026*
H3B	0.4198	0.6412	0.5376	0.026*
C4	0.56605 (17)	0.7637 (3)	0.70327 (17)	0.0233 (4)
H4A	0.6485	0.7151	0.7754	0.028*
H4B	0.6062	0.8588	0.6441	0.028*
C5	0.45413 (18)	0.8672 (3)	0.77210 (17)	0.0231 (4)
H5A	0.3771	0.9276	0.7000	0.028*
H5B	0.5034	0.9741	0.8326	0.028*
C6	0.38279 (17)	0.7232 (3)	0.85852 (16)	0.0213 (3)
H6A	0.3068	0.7934	0.8977	0.026*
H6B	0.4583	0.6737	0.9367	0.026*
C7	0.24625 (16)	0.4029 (2)	0.85586 (15)	0.0179 (3)
H7	0.2975	0.3801	0.9482	0.021*
C8	0.12236 (16)	0.3030 (2)	0.81294 (15)	0.0159 (3)
C9	0.02946 (18)	0.1295 (3)	0.60546 (16)	0.0219 (4)
H9A	0.1303	0.0932	0.5961	0.026*
H9B	−0.0320	0.1394	0.5111	0.026*
C10	−0.03310 (18)	−0.0344 (3)	0.68690 (17)	0.0220 (3)
H10A	−0.1217	−0.0933	0.6282	0.026*
H10B	0.0410	−0.1399	0.7132	0.026*
C11	−0.07289 (16)	0.0569 (2)	0.81812 (16)	0.0190 (3)
H11	−0.1119	−0.0451	0.8748	0.023*
C12	0.06546 (17)	0.1513 (2)	0.89894 (16)	0.0180 (3)
C13	−0.18536 (16)	0.2235 (3)	0.77418 (16)	0.0191 (3)
H13A	−0.2090	0.2879	0.8574	0.023*
H13B	−0.2773	0.1686	0.7185	0.023*
C14	−0.11873 (16)	0.3764 (3)	0.68726 (16)	0.0191 (3)
H14A	−0.1814	0.3848	0.5934	0.023*
H14B	−0.1181	0.5078	0.7313	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0164 (6)	0.0199 (7)	0.0134 (6)	−0.0022 (5)	0.0015 (4)	0.0001 (5)
O1	0.0301 (6)	0.0271 (7)	0.0182 (5)	−0.0032 (5)	−0.0005 (4)	0.0068 (5)
C1	0.0163 (7)	0.0162 (8)	0.0171 (7)	−0.0019 (6)	0.0015 (5)	0.0006 (6)
C2	0.0228 (7)	0.0162 (8)	0.0244 (8)	−0.0005 (6)	0.0069 (6)	−0.0011 (7)
C3	0.0200 (7)	0.0231 (8)	0.0229 (8)	−0.0014 (7)	0.0067 (6)	0.0001 (7)
C4	0.0194 (7)	0.0250 (9)	0.0244 (8)	−0.0058 (7)	0.0017 (6)	0.0043 (7)
C5	0.0286 (8)	0.0167 (8)	0.0223 (8)	−0.0053 (7)	0.0012 (6)	−0.0005 (7)
C6	0.0240 (8)	0.0190 (8)	0.0207 (8)	−0.0034 (7)	0.0041 (6)	−0.0022 (7)
C7	0.0183 (7)	0.0188 (8)	0.0157 (7)	0.0012 (6)	0.0014 (5)	0.0012 (6)
C8	0.0159 (7)	0.0163 (7)	0.0155 (7)	0.0009 (6)	0.0028 (5)	0.0011 (6)
C9	0.0220 (8)	0.0262 (9)	0.0179 (7)	−0.0025 (7)	0.0052 (6)	−0.0052 (7)
C10	0.0219 (7)	0.0190 (8)	0.0247 (8)	−0.0015 (7)	0.0037 (6)	−0.0044 (7)
C11	0.0221 (7)	0.0157 (8)	0.0200 (7)	−0.0036 (6)	0.0059 (6)	0.0008 (6)
C12	0.0207 (7)	0.0158 (7)	0.0178 (7)	0.0000 (6)	0.0047 (6)	0.0016 (6)
C13	0.0175 (7)	0.0199 (8)	0.0208 (7)	−0.0026 (6)	0.0059 (6)	−0.0023 (6)
C14	0.0167 (7)	0.0193 (8)	0.0208 (7)	−0.0007 (6)	0.0025 (5)	0.0023 (7)

Geometric parameters (Å, º)

N1—C8	1.4492 (18)	C6—H6A	0.9900
N1—C9	1.481 (2)	C6—H6B	0.9900
N1—C14	1.4826 (19)	C7—C8	1.328 (2)
O1—C12	1.2200 (19)	C7—H7	0.9500
C1—C7	1.498 (2)	C8—C12	1.494 (2)
C1—C6	1.532 (2)	C9—C10	1.549 (2)
C1—C2	1.540 (2)	C9—H9A	0.9900
C1—H1	1.0000	C9—H9B	0.9900
C2—C3	1.530 (2)	C10—C11	1.542 (2)
C2—H2A	0.9900	C10—H10A	0.9900
C2—H2B	0.9900	C10—H10B	0.9900
C3—C4	1.524 (2)	C11—C12	1.511 (2)
C3—H3A	0.9900	C11—C13	1.540 (2)
C3—H3B	0.9900	C11—H11	1.0000
C4—C5	1.520 (2)	C13—C14	1.549 (2)
C4—H4A	0.9900	C13—H13A	0.9900
C4—H4B	0.9900	C13—H13B	0.9900
C5—C6	1.529 (2)	C14—H14A	0.9900
C5—H5A	0.9900	C14—H14B	0.9900
C5—H5B	0.9900
C8—N1—C9	107.57 (12)	C8—C7—C1	125.57 (13)
C8—N1—C14	108.71 (11)	C8—C7—H7	117.2
C9—N1—C14	108.42 (12)	C1—C7—H7	117.2
C7—C1—C6	111.94 (12)	C7—C8—N1	122.95 (13)
C7—C1—C2	109.89 (13)	C7—C8—C12	123.52 (13)
C6—C1—C2	110.43 (12)	N1—C8—C12	113.46 (12)
C7—C1—H1	108.2	N1—C9—C10	112.08 (12)
C6—C1—H1	108.2	N1—C9—H9A	109.2
C2—C1—H1	108.2	C10—C9—H9A	109.2
C3—C2—C1	110.96 (13)	N1—C9—H9B	109.2
C3—C2—H2A	109.4	C10—C9—H9B	109.2
C1—C2—H2A	109.4	H9A—C9—H9B	107.9
C3—C2—H2B	109.4	C11—C10—C9	108.83 (13)
C1—C2—H2B	109.4	C11—C10—H10A	109.9
H2A—C2—H2B	108.0	C9—C10—H10A	109.9
C4—C3—C2	111.31 (13)	C11—C10—H10B	109.9
C4—C3—H3A	109.4	C9—C10—H10B	109.9
C2—C3—H3A	109.4	H10A—C10—H10B	108.3
C4—C3—H3B	109.4	C12—C11—C13	107.09 (13)
C2—C3—H3B	109.4	C12—C11—C10	106.88 (12)
H3A—C3—H3B	108.0	C13—C11—C10	108.74 (12)
C5—C4—C3	110.85 (13)	C12—C11—H11	111.3
C5—C4—H4A	109.5	C13—C11—H11	111.3
C3—C4—H4A	109.5	C10—C11—H11	111.3
C5—C4—H4B	109.5	O1—C12—C8	124.32 (14)
C3—C4—H4B	109.5	O1—C12—C11	125.01 (15)
H4A—C4—H4B	108.1	C8—C12—C11	110.66 (12)
C4—C5—C6	111.33 (14)	C11—C13—C14	108.84 (12)
C4—C5—H5A	109.4	C11—C13—H13A	109.9
C6—C5—H5A	109.4	C14—C13—H13A	109.9
C4—C5—H5B	109.4	C11—C13—H13B	109.9
C6—C5—H5B	109.4	C14—C13—H13B	109.9
H5A—C5—H5B	108.0	H13A—C13—H13B	108.3
C5—C6—C1	111.46 (13)	N1—C14—C13	112.08 (13)
C5—C6—H6A	109.3	N1—C14—H14A	109.2
C1—C6—H6A	109.3	C13—C14—H14A	109.2
C5—C6—H6B	109.3	N1—C14—H14B	109.2
C1—C6—H6B	109.3	C13—C14—H14B	109.2
H6A—C6—H6B	108.0	H14A—C14—H14B	107.9
C7—C1—C2—C3	−179.34 (12)	C14—N1—C9—C10	−59.21 (16)
C6—C1—C2—C3	−55.37 (17)	N1—C9—C10—C11	−0.08 (18)
C1—C2—C3—C4	56.28 (17)	C9—C10—C11—C12	−57.08 (17)
C2—C3—C4—C5	−56.41 (18)	C9—C10—C11—C13	58.22 (16)
C3—C4—C5—C6	56.03 (18)	C7—C8—C12—O1	2.5 (2)
C4—C5—C6—C1	−55.96 (18)	N1—C8—C12—O1	179.55 (16)
C7—C1—C6—C5	178.05 (13)	C7—C8—C12—C11	−176.92 (15)
C2—C1—C6—C5	55.26 (17)	N1—C8—C12—C11	0.08 (18)
C6—C1—C7—C8	142.91 (16)	C13—C11—C12—O1	122.34 (17)
C2—C1—C7—C8	−94.00 (18)	C10—C11—C12—O1	−121.26 (18)
C1—C7—C8—N1	−0.1 (2)	C13—C11—C12—C8	−58.20 (15)
C1—C7—C8—C12	176.60 (14)	C10—C11—C12—C8	58.20 (16)
C9—N1—C8—C7	117.95 (16)	C12—C11—C13—C14	58.06 (15)
C14—N1—C8—C7	−124.84 (16)	C10—C11—C13—C14	−57.11 (16)
C9—N1—C8—C12	−59.07 (15)	C8—N1—C14—C13	−56.26 (16)
C14—N1—C8—C12	58.13 (16)	C9—N1—C14—C13	60.40 (15)
C8—N1—C9—C10	58.18 (16)	C11—C13—C14—N1	−1.84 (17)