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The title compound, C15H17NO, was synthesized by base-catalyzed condensation of 4-methyl­benzaldehyde with 1-aza­bicyclo­[2.2.2]octan-3-one and crystallization of the product from ethyl acetate. The geometry of the C=C bond is Z.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048963/om2071sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048963/om2071Isup2.hkl
Contains datablock I

CCDC reference: 630213

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.047
  • wR factor = 0.128
  • Data-to-parameter ratio = 10.3

checkCIF/PLATON results

No syntax errors found



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 1602 Count of symmetry unique reflns 1601 Completeness (_total/calc) 100.06% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1 Fraction of Friedel pairs measured 0.001 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 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 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: SHELXL97 and local procedures.

(Z)-2-(4-Methylbenzylidene)-1-azabicyclo[2.2.2]octan-3-one top
Crystal data top
C15H17NOF(000) = 488
Mr = 227.30Dx = 1.271 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1619 reflections
a = 5.8527 (2) Åθ = 1.0–27.5°
b = 9.9840 (3) ŵ = 0.08 mm1
c = 20.3309 (6) ÅT = 90 K
V = 1188.00 (6) Å3Block, yellow
Z = 40.25 × 0.20 × 0.20 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
1602 independent reflections
Radiation source: fine-focus sealed tube1262 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 18 pixels mm-1θmax = 27.5°, θmin = 2.0°
ω scans at fixed χ = 55°h = 77
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
k = 1212
Tmin = 0.980, Tmax = 0.982l = 2626
2724 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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0819P)2]
where P = (Fo2 + 2Fc2)/3
1602 reflections(Δ/σ)max < 0.001
155 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.26 e Å3
Special details top

Experimental. 1H NMR (CDCl3, δ, p.p.m.): 2.03 (m, 4H), 2.37 (s, 3H), 2.62 (p, 1H), 2.98 (p, 2H), 3.13 (p, 2H), 7.00 (s, 1H), 7.18 (d, 2H), 7.94 (d, 2H); 13C NMR (CDCl3, δ, p.p.m.): 21.6, 26.0, 40.3, 47.5, 125.1, 129.1, 131.1, 132.0, 139.8, 143.9, 206.2.

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
C10.5858 (4)0.5276 (2)0.38226 (11)0.0167 (5)
C20.4250 (4)0.6220 (2)0.36096 (11)0.0191 (5)
H20.28860.63530.38540.023*
C30.4638 (5)0.6959 (2)0.30453 (12)0.0220 (6)
H30.35180.75850.29050.026*
C40.6636 (4)0.6809 (2)0.26760 (11)0.0202 (6)
C50.8206 (5)0.5861 (2)0.28855 (11)0.0214 (6)
H50.95710.57350.26400.026*
C60.7839 (5)0.5088 (2)0.34456 (11)0.0190 (6)
H60.89310.44340.35730.023*
C70.5558 (5)0.4446 (2)0.44123 (11)0.0172 (5)
H70.63210.36070.44050.021*
C80.4368 (4)0.4703 (2)0.49567 (11)0.0156 (5)
N90.3166 (4)0.5927 (2)0.50949 (9)0.0178 (5)
C100.0731 (4)0.5604 (3)0.52208 (12)0.0206 (6)
H10A0.00500.52120.48190.025*
H10B0.01080.64390.53240.025*
C110.0451 (5)0.4603 (2)0.57997 (12)0.0202 (6)
H11A0.04760.50140.61530.024*
H11B0.03420.37850.56460.024*
C120.2845 (5)0.4238 (2)0.60652 (12)0.0205 (6)
H120.27400.35730.64320.025*
O130.5189 (3)0.26066 (16)0.55027 (8)0.0217 (4)
C130.4252 (4)0.3700 (2)0.55038 (11)0.0165 (5)
C140.4016 (5)0.5535 (2)0.62937 (12)0.0226 (6)
H14A0.55760.53360.64540.027*
H14B0.31380.59420.66590.027*
C150.4133 (5)0.6524 (2)0.57049 (11)0.0211 (6)
H15A0.32750.73480.58160.025*
H15B0.57450.67770.56260.025*
C160.7073 (5)0.7674 (3)0.20801 (12)0.0259 (6)
H16A0.78660.84940.22150.039*
H16B0.56140.79090.18730.039*
H16C0.80220.71820.17650.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0204 (12)0.0151 (11)0.0148 (11)0.0009 (11)0.0002 (10)0.0057 (10)
C20.0189 (12)0.0203 (12)0.0181 (12)0.0008 (12)0.0014 (11)0.0020 (10)
C30.0271 (14)0.0188 (12)0.0202 (12)0.0036 (12)0.0034 (12)0.0012 (11)
C40.0257 (14)0.0180 (12)0.0168 (11)0.0042 (12)0.0018 (12)0.0020 (11)
C50.0205 (12)0.0256 (14)0.0181 (12)0.0011 (12)0.0020 (12)0.0025 (11)
C60.0207 (13)0.0173 (12)0.0189 (12)0.0006 (11)0.0001 (11)0.0022 (11)
C70.0177 (12)0.0132 (11)0.0206 (12)0.0013 (11)0.0002 (11)0.0017 (10)
C80.0140 (11)0.0132 (11)0.0195 (12)0.0000 (11)0.0016 (10)0.0003 (10)
N90.0198 (10)0.0165 (11)0.0173 (10)0.0046 (10)0.0011 (10)0.0007 (9)
C100.0153 (12)0.0245 (14)0.0220 (13)0.0026 (12)0.0004 (11)0.0007 (11)
C110.0179 (13)0.0184 (12)0.0244 (13)0.0003 (11)0.0040 (11)0.0022 (11)
C120.0234 (14)0.0208 (13)0.0173 (12)0.0013 (12)0.0021 (12)0.0040 (11)
O130.0245 (10)0.0155 (8)0.0250 (9)0.0018 (8)0.0003 (9)0.0010 (8)
C130.0146 (11)0.0168 (12)0.0181 (12)0.0044 (11)0.0008 (11)0.0025 (11)
C140.0257 (14)0.0224 (13)0.0196 (13)0.0026 (13)0.0000 (12)0.0049 (10)
C150.0235 (14)0.0176 (13)0.0222 (13)0.0004 (12)0.0006 (12)0.0042 (11)
C160.0326 (15)0.0250 (14)0.0200 (12)0.0017 (14)0.0011 (13)0.0008 (11)
Geometric parameters (Å, º) top
C1—C21.400 (3)C10—C111.553 (3)
C1—C61.402 (3)C10—H10A0.9900
C1—C71.468 (3)C10—H10B0.9900
C2—C31.383 (3)C11—C121.545 (4)
C2—H20.9500C11—H11A0.9900
C3—C41.397 (4)C11—H11B0.9900
C3—H30.9500C12—C131.507 (3)
C4—C51.386 (3)C12—C141.537 (3)
C4—C161.510 (3)C12—H121.0000
C5—C61.392 (3)O13—C131.221 (3)
C5—H50.9500C14—C151.553 (3)
C6—H60.9500C14—H14A0.9900
C7—C81.332 (3)C14—H14B0.9900
C7—H70.9500C15—H15A0.9900
C8—N91.438 (3)C15—H15B0.9900
C8—C131.498 (3)C16—H16A0.9800
N9—C101.484 (3)C16—H16B0.9800
N9—C151.488 (3)C16—H16C0.9800
C2—C1—C6118.4 (2)C12—C11—C10108.71 (19)
C2—C1—C7123.5 (2)C12—C11—H11A109.9
C6—C1—C7118.0 (2)C10—C11—H11A109.9
C3—C2—C1120.3 (2)C12—C11—H11B109.9
C3—C2—H2119.8C10—C11—H11B109.9
C1—C2—H2119.8H11A—C11—H11B108.3
C2—C3—C4121.7 (2)C13—C12—C14106.6 (2)
C2—C3—H3119.1C13—C12—C11108.4 (2)
C4—C3—H3119.1C14—C12—C11108.1 (2)
C5—C4—C3117.6 (2)C13—C12—H12111.2
C5—C4—C16121.7 (2)C14—C12—H12111.2
C3—C4—C16120.8 (2)C11—C12—H12111.2
C4—C5—C6121.8 (2)O13—C13—C8125.1 (2)
C4—C5—H5119.1O13—C13—C12124.5 (2)
C6—C5—H5119.1C8—C13—C12110.4 (2)
C5—C6—C1120.1 (2)C12—C14—C15108.80 (19)
C5—C6—H6120.0C12—C14—H14A109.9
C1—C6—H6120.0C15—C14—H14A109.9
C8—C7—C1129.2 (2)C12—C14—H14B109.9
C8—C7—H7115.4C15—C14—H14B109.9
C1—C7—H7115.4H14A—C14—H14B108.3
C7—C8—N9125.5 (2)N9—C15—C14111.78 (19)
C7—C8—C13120.8 (2)N9—C15—H15A109.3
N9—C8—C13113.62 (19)C14—C15—H15A109.3
C8—N9—C10108.6 (2)N9—C15—H15B109.3
C8—N9—C15108.50 (19)C14—C15—H15B109.3
C10—N9—C15108.0 (2)H15A—C15—H15B107.9
N9—C10—C11111.8 (2)C4—C16—H16A109.5
N9—C10—H10A109.2C4—C16—H16B109.5
C11—C10—H10A109.2H16A—C16—H16B109.5
N9—C10—H10B109.2C4—C16—H16C109.5
C11—C10—H10B109.2H16A—C16—H16C109.5
H10A—C10—H10B107.9H16B—C16—H16C109.5
C6—C1—C2—C30.9 (3)C8—N9—C10—C1158.0 (3)
C7—C1—C2—C3179.4 (2)C15—N9—C10—C1159.5 (3)
C1—C2—C3—C40.9 (4)N9—C10—C11—C120.5 (3)
C2—C3—C4—C51.7 (4)C10—C11—C12—C1356.0 (2)
C2—C3—C4—C16177.0 (2)C10—C11—C12—C1459.2 (3)
C3—C4—C5—C60.6 (4)C7—C8—C13—O130.0 (4)
C16—C4—C5—C6178.1 (2)N9—C8—C13—O13178.1 (2)
C4—C5—C6—C11.2 (4)C7—C8—C13—C12178.9 (2)
C2—C1—C6—C52.0 (3)N9—C8—C13—C120.8 (3)
C7—C1—C6—C5179.4 (2)C14—C12—C13—O13119.7 (2)
C2—C1—C7—C827.5 (4)C11—C12—C13—O13124.1 (2)
C6—C1—C7—C8154.0 (3)C14—C12—C13—C859.3 (3)
C1—C7—C8—N93.1 (4)C11—C12—C13—C856.9 (3)
C1—C7—C8—C13179.0 (2)C13—C12—C14—C1558.5 (3)
C7—C8—N9—C10122.8 (3)C11—C12—C14—C1557.8 (3)
C13—C8—N9—C1059.2 (3)C8—N9—C15—C1456.5 (3)
C7—C8—N9—C15120.0 (3)C10—N9—C15—C1461.0 (3)
C13—C8—N9—C1558.0 (2)C12—C14—C15—N91.8 (3)
 

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