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Crystals of the title compound, C12H13NOS, were prepared by base-catalyzed reaction of thio­phene-2-carboxaldehyde with 1-aza­bicyclo­[2.2.2]octan-3-one and subsequent crystallization of the product from ethyl acetate. The olefinic bond connecting the 2-thienyl and 1-aza­bicyclo­[2.2.2]octan-3-one moieties has Z geometry. No thienyl ring flip is observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049403/om2072sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049403/om2072Isup2.hkl
Contains datablock I

CCDC reference: 630214

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.036
  • wR factor = 0.091
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C12 H13 N O S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker–Nonius, 2004); cell refinement: SAINT (Bruker–Nonius, 2004); data reduction: SAINT; 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-(Thiophen-2-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one top
Crystal data top
C12H13NOSF(000) = 464
Mr = 219.29Dx = 1.383 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ynCell parameters from 5645 reflections
a = 11.0171 (2) Åθ = 2.7–68.0°
b = 5.9253 (1) ŵ = 2.48 mm1
c = 16.1888 (2) ÅT = 90 K
β = 94.640 (1)°Block, yellow
V = 1053.34 (3) Å30.15 × 0.08 × 0.08 mm
Z = 4
Data collection top
Bruker–Nonius X8 Proteum
diffractometer
1880 independent reflections
Radiation source: fine-focus rotating anode1845 reflections with I > 2σ(I)
Graded multilayer optics monochromatorRint = 0.031
Detector resolution: 18 pixels mm-1θmax = 68.0°, θmin = 4.7°
ω scans at fixed χ = 55°h = 1313
Absorption correction: multi-scan
(SADABS in APEX2; Bruker–Nonius, 2004)
k = 77
Tmin = 0.657, Tmax = 0.836l = 1918
11773 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.091 w = 1/[σ2(Fo2) + (0.0559P)2 + 0.4238P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
1880 reflectionsΔρmax = 0.29 e Å3
137 parametersΔρmin = 0.36 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0209 (12)
Special details top

Experimental. 1H NMR (CDCl3): δ 2.02 (m, 4H), 2.63 (p, 1H), 2.93 (p, 2H), 3.18 (p, 2H), 7.04 (t, 1H), 7.31 (d, 1H), 7.35 (1H, d), 7.54 (1H, d). 13C NMR (CDCl3): δ 26.24, 40.57, 47.34, 119.72, 126.49, 133.43, 133.49, 136.85, 141.48, 204.89.

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
S10.00010 (3)0.00858 (5)0.24150 (2)0.01743 (17)
N10.18759 (10)0.04388 (19)0.35875 (7)0.0162 (3)
O10.14829 (9)0.29255 (17)0.54515 (6)0.0223 (3)
C10.03102 (11)0.2167 (2)0.31553 (8)0.0156 (3)
C20.10350 (12)0.1220 (2)0.17941 (8)0.0199 (3)
H20.12020.06050.12730.024*
C30.15901 (12)0.3098 (2)0.21300 (8)0.0200 (3)
H30.21860.39430.18710.024*
C40.11756 (11)0.3643 (2)0.29114 (8)0.0181 (3)
H40.14660.49000.32340.022*
C50.02847 (11)0.2360 (2)0.39141 (8)0.0163 (3)
H50.00510.34260.43070.020*
C60.12575 (11)0.1206 (2)0.41263 (8)0.0158 (3)
C70.20399 (13)0.2527 (2)0.40660 (8)0.0207 (3)
H7A0.12330.31000.42850.025*
H7B0.24270.36940.36940.025*
C80.28423 (13)0.2113 (2)0.47981 (9)0.0220 (3)
H8A0.36240.29330.47010.026*
H8B0.24190.26700.53210.026*
C90.30797 (12)0.0440 (2)0.48599 (8)0.0184 (3)
H90.35290.08020.53560.022*
C100.18689 (12)0.1668 (2)0.48923 (8)0.0166 (3)
C110.38021 (12)0.1211 (2)0.40535 (8)0.0197 (3)
H11A0.39030.28710.40560.024*
H11B0.46210.05110.40100.024*
C120.30920 (12)0.0486 (2)0.33058 (8)0.0181 (3)
H12A0.35660.06720.29780.022*
H12B0.29910.18060.29430.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0185 (2)0.0168 (2)0.0171 (2)0.00049 (11)0.00228 (15)0.00383 (11)
N10.0172 (6)0.0146 (5)0.0166 (6)0.0009 (4)0.0006 (4)0.0021 (4)
O10.0259 (5)0.0232 (5)0.0181 (5)0.0044 (4)0.0038 (4)0.0057 (4)
C10.0145 (6)0.0159 (6)0.0163 (6)0.0018 (5)0.0002 (5)0.0012 (5)
C20.0195 (7)0.0249 (7)0.0155 (6)0.0033 (5)0.0030 (5)0.0014 (6)
C30.0175 (6)0.0248 (7)0.0181 (7)0.0004 (5)0.0035 (5)0.0019 (5)
C40.0169 (6)0.0189 (7)0.0185 (6)0.0000 (5)0.0009 (5)0.0012 (5)
C50.0170 (6)0.0158 (6)0.0158 (6)0.0018 (5)0.0005 (5)0.0014 (5)
C60.0174 (6)0.0146 (6)0.0151 (6)0.0008 (5)0.0003 (5)0.0010 (5)
C70.0253 (7)0.0137 (7)0.0230 (7)0.0005 (5)0.0009 (5)0.0002 (5)
C80.0267 (7)0.0186 (7)0.0206 (7)0.0048 (6)0.0018 (5)0.0039 (5)
C90.0199 (7)0.0202 (7)0.0157 (7)0.0029 (5)0.0042 (5)0.0002 (5)
C100.0192 (6)0.0144 (6)0.0164 (6)0.0010 (5)0.0022 (5)0.0017 (5)
C110.0170 (6)0.0216 (7)0.0206 (7)0.0002 (5)0.0024 (5)0.0012 (5)
C120.0178 (7)0.0198 (6)0.0164 (7)0.0005 (5)0.0001 (5)0.0006 (5)
Geometric parameters (Å, º) top
S1—C21.7178 (13)C6—C101.4838 (17)
S1—C11.7342 (13)C7—C81.5542 (19)
N1—C61.4417 (16)C7—H7A0.9900
N1—C71.4788 (17)C7—H7B0.9900
N1—C121.4847 (17)C8—C91.5396 (19)
O1—C101.2219 (16)C8—H8A0.9900
C1—C41.3751 (19)C8—H8B0.9900
C1—C51.4429 (18)C9—C101.5169 (18)
C2—C31.361 (2)C9—C111.5422 (18)
C2—H20.9500C9—H91.0000
C3—C41.4166 (18)C11—C121.5539 (18)
C3—H30.9500C11—H11A0.9900
C4—H40.9500C11—H11B0.9900
C5—C61.3394 (19)C12—H12A0.9900
C5—H50.9500C12—H12B0.9900
C2—S1—C191.29 (6)C9—C8—C7108.35 (11)
C6—N1—C7108.69 (10)C9—C8—H8A110.0
C6—N1—C12107.86 (10)C7—C8—H8A110.0
C7—N1—C12108.93 (10)C9—C8—H8B110.0
C4—C1—C5124.55 (12)C7—C8—H8B110.0
C4—C1—S1110.90 (10)H8A—C8—H8B108.4
C5—C1—S1124.52 (10)C10—C9—C8108.67 (11)
C3—C2—S1112.60 (10)C10—C9—C11106.22 (11)
C3—C2—H2123.7C8—C9—C11108.35 (11)
S1—C2—H2123.7C10—C9—H9111.1
C2—C3—C4112.09 (12)C8—C9—H9111.1
C2—C3—H3124.0C11—C9—H9111.1
C4—C3—H3124.0O1—C10—C6125.27 (12)
C1—C4—C3113.11 (12)O1—C10—C9124.79 (12)
C1—C4—H4123.4C6—C10—C9109.87 (11)
C3—C4—H4123.4C9—C11—C12108.65 (11)
C6—C5—C1127.29 (12)C9—C11—H11A110.0
C6—C5—H5116.4C12—C11—H11A110.0
C1—C5—H5116.4C9—C11—H11B110.0
C5—C6—N1122.60 (12)C12—C11—H11B110.0
C5—C6—C10123.15 (12)H11A—C11—H11B108.3
N1—C6—C10113.97 (11)N1—C12—C11111.19 (11)
N1—C7—C8111.62 (11)N1—C12—H12A109.4
N1—C7—H7A109.3C11—C12—H12A109.4
C8—C7—H7A109.3N1—C12—H12B109.4
N1—C7—H7B109.3C11—C12—H12B109.4
C8—C7—H7B109.3H12A—C12—H12B108.0
H7A—C7—H7B108.0
C2—S1—C1—C40.19 (10)N1—C7—C8—C97.20 (15)
C2—S1—C1—C5178.54 (11)C7—C8—C9—C1052.17 (14)
C1—S1—C2—C30.22 (11)C7—C8—C9—C1162.83 (14)
S1—C2—C3—C40.19 (15)C5—C6—C10—O19.2 (2)
C5—C1—C4—C3178.46 (12)N1—C6—C10—O1176.83 (12)
S1—C1—C4—C30.12 (15)C5—C6—C10—C9167.94 (12)
C2—C3—C4—C10.05 (17)N1—C6—C10—C96.06 (15)
C4—C1—C5—C6168.73 (13)C8—C9—C10—O1122.13 (14)
S1—C1—C5—C69.4 (2)C11—C9—C10—O1121.49 (14)
C1—C5—C6—N11.0 (2)C8—C9—C10—C660.74 (13)
C1—C5—C6—C10174.52 (12)C11—C9—C10—C655.63 (13)
C7—N1—C6—C5130.97 (13)C10—C9—C11—C1262.04 (13)
C12—N1—C6—C5111.08 (14)C8—C9—C11—C1254.55 (14)
C7—N1—C6—C1055.00 (14)C6—N1—C12—C1153.67 (14)
C12—N1—C6—C1062.96 (13)C7—N1—C12—C1164.14 (14)
C6—N1—C7—C861.81 (14)C9—C11—C12—N17.49 (15)
C12—N1—C7—C855.47 (14)
 

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