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The crystal structure of C12H13NOS, which was obtained in a base-catalysed condensation reaction of thio­phene-3-carbox­aldehyde with 1-aza-bi­cyclo­[2.2.2]­octan-3-one, is presented. The title compound, which contains a double bond connecting an aza­bicyclic ring system to a thio­phen-3-yl­methyl­ene moiety, crystallizes from solution in methanol and has a thienyl ring-flip disorder.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019007/om6170sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019007/om6170Isup2.hkl
Contains datablock I

CCDC reference: 225709

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.122
  • Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT301_ALERT_3_C Main Residue Disorder ......................... 12.00 Perc. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 7.70 Deg. C5' -C2 -S1 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 8.10 Deg. C5 -C4 -S1' 1.555 1.555 1.555 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 5 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 2 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

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, 1994); software used to prepare material for publication: SHELX97 (Sheldrick, 1997) and local procedures.

(Z)-2-Thiophen-3-ylmethylene-1-aza-bicyclo[2.2.2]octan-3-one top
Crystal data top
C12H13NOSF(000) = 464
Mr = 219.29Dx = 1.363 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.321 (1) ÅCell parameters from 6483 reflections
b = 5.8790 (6) Åθ = 1.0–27.5°
c = 16.100 (2) ŵ = 0.27 mm1
β = 94.058 (10)°T = 173 K
V = 1068.9 (2) Å3Rod, yellow
Z = 40.40 × 0.33 × 0.20 mm
Data collection top
Nonius KappaCCD
diffractometer
2452 independent reflections
Radiation source: fine-focus sealed tube1802 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
Detector resolution: 18 pixels mm-1θmax = 27.5°, θmin = 2.1°
ω scans at fixed χ = 55°h = 1414
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
k = 77
Tmin = 0.899, Tmax = 0.947l = 2020
7996 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)] = 0.045H-atom parameters constrained
wR(F2) = 0.122 w = 1/[σ2(Fo2) + (0.0604P)2 + 0.2115P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.002
2452 reflectionsΔρmax = 0.24 e Å3
143 parametersΔρmin = 0.25 e Å3
8 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.020 (3)
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*/UeqOcc. (<1)
S10.1702 (3)0.3427 (5)0.29234 (16)0.0389 (4)0.50
C5'0.1557 (11)0.317 (2)0.2840 (7)0.0389 (4)0.50
H5'0.21440.40590.30820.047*0.50
C20.11178 (15)0.3704 (3)0.20480 (11)0.0374 (4)
H20.13290.49210.16780.045*
C30.02826 (14)0.2065 (3)0.18579 (10)0.0296 (4)
C40.01283 (15)0.0427 (3)0.24936 (10)0.0333 (4)
H40.03950.08380.25020.040*
C50.0883 (8)0.0997 (15)0.3110 (4)0.0366 (3)0.50
H50.09400.01060.35980.044*0.50
S1'0.09402 (17)0.0817 (3)0.33130 (8)0.0366 (3)0.50
C60.03386 (14)0.2198 (3)0.11007 (10)0.0294 (4)
H60.00060.32090.06870.035*
C70.13123 (14)0.1097 (3)0.09042 (10)0.0272 (4)
N80.19491 (12)0.0516 (2)0.14457 (8)0.0304 (4)
C90.21488 (18)0.2604 (3)0.09625 (12)0.0415 (5)
H9A0.25600.37440.13320.050*
H9B0.13750.32520.07590.050*
C100.28946 (18)0.2139 (3)0.02131 (12)0.0440 (5)
H10A0.24720.26960.03070.053*
H10B0.36640.29400.02890.053*
C110.30970 (15)0.0440 (3)0.01581 (10)0.0351 (4)
H110.35270.08370.03440.042*
C120.37970 (16)0.1217 (3)0.09611 (10)0.0370 (4)
H12A0.45940.05150.10000.044*
H12B0.38930.28910.09580.044*
C130.31109 (15)0.0486 (3)0.17110 (10)0.0354 (4)
H13A0.29910.18260.20680.043*
H13B0.35860.06420.20470.043*
C140.19134 (15)0.1599 (3)0.01362 (10)0.0323 (4)
O150.15168 (12)0.2842 (2)0.04277 (7)0.0451 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0353 (9)0.0493 (8)0.0325 (7)0.0044 (5)0.0049 (5)0.0035 (6)
C5'0.0353 (9)0.0493 (8)0.0325 (7)0.0044 (5)0.0049 (5)0.0035 (6)
C20.0299 (9)0.0437 (11)0.0379 (10)0.0042 (8)0.0021 (8)0.0008 (8)
C30.0242 (8)0.0339 (9)0.0303 (9)0.0038 (7)0.0013 (6)0.0009 (7)
C40.0305 (9)0.0352 (10)0.0342 (9)0.0036 (8)0.0018 (7)0.0056 (7)
C50.0321 (5)0.0473 (6)0.0305 (8)0.0003 (4)0.0040 (6)0.0064 (6)
S1'0.0321 (5)0.0473 (6)0.0305 (8)0.0003 (4)0.0040 (6)0.0064 (6)
C60.0276 (9)0.0309 (9)0.0290 (9)0.0010 (7)0.0033 (7)0.0044 (7)
C70.0287 (9)0.0263 (9)0.0265 (8)0.0013 (7)0.0002 (6)0.0018 (6)
N80.0339 (8)0.0264 (7)0.0308 (7)0.0042 (6)0.0018 (6)0.0034 (6)
C90.0540 (11)0.0256 (9)0.0453 (11)0.0028 (9)0.0060 (9)0.0007 (8)
C100.0592 (13)0.0355 (10)0.0376 (11)0.0087 (9)0.0056 (9)0.0080 (8)
C110.0392 (10)0.0386 (10)0.0283 (9)0.0043 (8)0.0085 (7)0.0003 (7)
C120.0319 (9)0.0394 (10)0.0399 (10)0.0009 (8)0.0035 (7)0.0008 (8)
C130.0354 (10)0.0400 (10)0.0303 (9)0.0059 (8)0.0017 (7)0.0018 (8)
C140.0384 (10)0.0310 (9)0.0272 (9)0.0007 (8)0.0011 (7)0.0002 (7)
O150.0531 (8)0.0502 (8)0.0320 (7)0.0098 (7)0.0035 (6)0.0123 (6)
Geometric parameters (Å, º) top
S1—C21.607 (3)N8—C131.476 (2)
S1—C51.718 (8)N8—C91.480 (2)
C5'—C21.436 (10)C9—C101.545 (3)
C5'—S1'1.705 (11)C9—H9A0.9900
C5'—H5'0.9500C9—H9B0.9900
C2—C31.399 (2)C10—C111.537 (3)
C2—H20.9500C10—H10A0.9900
C3—C41.407 (2)C10—H10B0.9900
C3—C61.452 (2)C11—C141.501 (2)
C4—C51.395 (7)C11—C121.537 (2)
C4—S1'1.676 (2)C11—H111.0000
C4—H40.9500C12—C131.542 (2)
C5—H50.9500C12—H12A0.9900
C6—C71.335 (2)C12—H12B0.9900
C6—H60.9500C13—H13A0.9900
C7—N81.4456 (19)C13—H13B0.9900
C7—C141.483 (2)C14—O151.2255 (19)
C2—S1—C589.3 (2)N8—C9—H9A109.2
C2—C5'—S1'114.7 (7)C10—C9—H9A109.2
C2—C5'—H5'122.7N8—C9—H9B109.2
S1'—C5'—H5'122.7C10—C9—H9B109.2
C3—C2—C5'109.0 (4)H9A—C9—H9B107.9
C3—C2—S1116.65 (17)C11—C10—C9108.16 (14)
C5'—C2—S17.7 (5)C11—C10—H10A110.1
C3—C2—H2121.7C9—C10—H10A110.1
C5'—C2—H2129.3C11—C10—H10B110.1
S1—C2—H2121.7C9—C10—H10B110.1
C2—C3—C4111.30 (15)H10A—C10—H10B108.4
C2—C3—C6121.44 (15)C14—C11—C10108.21 (15)
C4—C3—C6127.22 (15)C14—C11—C12106.92 (14)
C5—C4—C3107.6 (3)C10—C11—C12108.34 (15)
C5—C4—S1'8.1 (4)C14—C11—H11111.1
C3—C4—S1'115.59 (15)C10—C11—H11111.1
C5—C4—H4126.2C12—C11—H11111.1
C3—C4—H4126.2C11—C12—C13108.51 (14)
S1'—C4—H4118.2C11—C12—H12A110.0
C4—C5—S1115.2 (4)C13—C12—H12A110.0
C4—C5—H5122.4C11—C12—H12B110.0
S1—C5—H5122.4C13—C12—H12B110.0
C4—S1'—C5'89.4 (4)H12A—C12—H12B108.4
C7—C6—C3129.04 (15)N8—C13—C12111.86 (13)
C7—C6—H6115.5N8—C13—H13A109.2
C3—C6—H6115.5C12—C13—H13A109.2
C6—C7—N8124.03 (15)N8—C13—H13B109.2
C6—C7—C14122.43 (14)C12—C13—H13B109.2
N8—C7—C14113.26 (13)H13A—C13—H13B107.9
C7—N8—C13107.99 (12)O15—C14—C7124.81 (16)
C7—N8—C9108.39 (13)O15—C14—C11124.58 (16)
C13—N8—C9108.48 (14)C7—C14—C11110.58 (13)
N8—C9—C10112.07 (14)
S1'—C5'—C2—C31.1 (10)C6—C7—N8—C13112.28 (17)
S1'—C5'—C2—S1173 (6)C14—C7—N8—C1361.85 (17)
C5—S1—C2—C31.2 (4)C6—C7—N8—C9130.39 (17)
C5—S1—C2—C5'5 (5)C14—C7—N8—C955.48 (17)
C5'—C2—C3—C40.2 (6)C7—N8—C9—C1060.80 (19)
S1—C2—C3—C40.7 (2)C13—N8—C9—C1056.22 (19)
C5'—C2—C3—C6178.3 (6)N8—C9—C10—C115.4 (2)
S1—C2—C3—C6177.40 (19)C9—C10—C11—C1453.67 (19)
C2—C3—C4—C50.4 (4)C9—C10—C11—C1261.91 (19)
C6—C3—C4—C5178.3 (4)C14—C11—C12—C1360.59 (18)
C2—C3—C4—S1'0.7 (2)C10—C11—C12—C1355.84 (18)
C6—C3—C4—S1'177.21 (15)C7—N8—C13—C1254.49 (18)
C3—C4—C5—S11.2 (7)C9—N8—C13—C1262.79 (17)
S1'—C4—C5—S1172 (4)C11—C12—C13—N85.7 (2)
C2—S1—C5—C41.4 (6)C6—C7—C14—O158.8 (3)
C5—C4—S1'—C5'6 (3)N8—C7—C14—O15176.96 (15)
C3—C4—S1'—C5'1.1 (5)C6—C7—C14—C11169.17 (15)
C2—C5'—S1'—C41.3 (9)N8—C7—C14—C115.06 (18)
C2—C3—C6—C7164.64 (16)C10—C11—C14—O15121.19 (18)
C4—C3—C6—C713.1 (3)C12—C11—C14—O15122.30 (18)
C3—C6—C7—N80.2 (3)C10—C11—C14—C760.82 (17)
C3—C6—C7—C14173.45 (15)C12—C11—C14—C755.69 (18)
 

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